Coloring composition, ink jet recording ink, ink jet recording method, and ink jet printer cartridge

ABSTRACT

Provided are a coloring composition including a compound represented Formula (1) shown in the specification and at least one compound selected from the group consisting of the compound represented by Formula (D) shown in the specification and the compound represented by Formula (E) shown in the specification, an ink jet recording ink including the coloring composition, an ink jet recording method using the ink jet recording ink, and an ink jet printer cartridge that is filled with the ink jet recording ink.

CROSS REFERENCE TO RELATED APPLICATION

This is a continuation of International Application No.PCT/JP2017/007214 filed on Feb. 24, 2017, and claims priority fromJapanese Patent Application No. 2016-032828 filed on Feb. 24, 2016 andpriority from Japanese Patent Application No. 2017-030496 filed on Feb.21, 2017, the entire disclosures of which are incorporated therein byreference.

BACKGROUND OF THE INVENTION 1. Field of the Invention

The present invention relates to a coloring composition, an ink jetrecording ink, an ink jet recording method, and an ink jet printercartridge.

2. Description of the Related Art

In the ink jet recording method, as is well-known in the related art,small ink droplets are jetted to be attached to a recording medium suchas paper to perform printing. In this printing method, a high-resolutionand high-quality image can be printed rapidly and simply using aninexpensive device. Particularly in color printing, recently, atechnique of the printing method has been developed as an image formingmethod capable of replacing photography.

For example, JP2013-133396A and WO2015/105108A describe an ink jetrecording ink including a xanthene compound.

SUMMARY OF THE INVENTION

However, in the dye field, further improvement of performance isrequired.

An object of the present invention is to provide: a coloring compositionwith which an image having excellent color, saturation, and adhesion(printing density) and having excellent light fastness, ozone fastness,and moisture resistance can be formed and that has excellent jettingstability in an ink jet printer; an ink jet recording ink including thecoloring composition; an ink jet recording method using the ink jetrecording ink; and an ink jet printer cartridge that is filled with theink jet recording ink.

The present inventors performed a thorough investigation and found thatthe above-described object can be achieved by the following means. Inthe present invention, by using a compound represented by Formula (1)and at least one selected from the group consisting of a compoundrepresented by Formula (D) and a compound represented by Formula (E) incombination, high adhesion (printing density) and image fastness (lightfastness, ozone fastness, and moisture resistance) can be realized whilereducing the dye concentration (contributing to improvement of jettingstability of the ink) in the coloring composition (ink). Thisconfiguration is preferable because, by using different coloring agentmother nuclei having excellent color, saturation, and high adhesion incombination, the adhesion and the image fastness can be satisfied at ahigh level as compared to a case where one of the coloring agent mothernuclei is used alone.

The detailed reason is not clear but is presumed to be that, in a casewhere a xanthene dye represented by Formula (1) and at least oneanthrapyridone dye selected from the group consisting of a compoundrepresented by Formula (D) and a compound represented by Formula (E) arepresent together (for example, in an ink jet recording ink, or an inkjet printed material prepared using an ink jet recording method; onpaper for ink jet recording), a physicochemical interaction hardlyoccurs, and required performance can be realized without causing a largedrawback such as deterioration in light fastness or deterioration in inkjetting stability.

<1> A coloring composition comprising:

a compound represented by the following Formula (1); and

at least one compound selected from the group consisting of a compoundrepresented by the following Formula (D) and a compound represented bythe following Formula (E),

in Formula (1), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group,

R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ eachindependently represent a hydrogen atom or a substituent,

R², R³, R⁷, and R⁸ each independently represent a hydrogen atom, analkyl group, or a substituent represented by the following Formula (A),and

at least one of R², R³, R⁷, or R⁸ represents a substituent representedby the following Formula (A),

in Formula (A), X represents a substituent represented by the followingFormula (X1), (X2), or (X3), and

* represents a direct bond to a benzene ring,

in Formula (X1), R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ each independentlyrepresent a hydrogen atom or a substituent,

R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ satisfy the following condition (i) or(ii),

* represents a direct bond to a sulfur atom,

the condition (i): at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represents a hydroxyl group and at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴,or R⁴⁰⁵ represents a carboxyl group, and

the condition (ii): at least two of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represent a carboxyl group,

in Formula (X2), R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ eachindependently represent a hydrogen atom or a substituent,

R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ satisfy the followingcondition (iii) or (iv),

* represents a direct bond to a sulfur atom,

the condition (iii): at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶,and R⁵⁰⁷ represents a hydroxyl group and at least one of R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ represents a carboxyl group, and

the condition (iv): at least two of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶,and R⁵⁰⁷ represent a carboxyl group,

in Formula (X3), R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ eachindependently represent a hydrogen atom or a substituent,

R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ satisfy the followingcondition (v) or (vi),

* represents a direct bond to a sulfur atom,

the condition (v): at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,and R⁶⁰⁷ represents a hydroxyl group and at least one of R⁶⁰¹, R⁶⁰²,R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ represents a carboxyl group, and

the condition (vi): at least two of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,and R⁶⁰⁷ represent a carboxyl group,

in Formula (D), R₂₁ and R₂₂ each independently represent a hydrogen atomor a substituted or unsubstituted alkyl group,

Y₂₁ and Y₂₂ each independently represent a chlorine atom, a hydroxylgroup, a substituted or unsubstituted amino group, an alkoxy group, asubstituted or unsubstituted phenoxy group, or a substituted orunsubstituted naphthyloxy group,

Xd represents a divalent linking group,

M⁴ represents a hydrogen atom or a counter cation, and

M⁴′s may be the same as or different from each other,

in Formula (E), R₃₁ represents a hydrogen atom or a substituted orunsubstituted alkyl group,

Y₃₁ represents a chlorine atom, a hydroxyl group, a substituted orunsubstituted amino group, or a morpholino group,

M⁵ represents a hydrogen atom or a counter cation.

M⁵′s may be the same as or different from each other, and

X₃₁ represents a group represented by the following Formula (E-1), and

in Formula (E-1), R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ each independentlyrepresent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or—COOM′ (M′ represents a hydrogen atom or a counter cation),

at least one of R₃₂, R₃₃, R₃₄, R₃₅, or R₃₆ represents an alkyl grouphaving 1 to 8 carbon atoms or —COOM′, and

* represents a direct bond to a carbon atom.

<2> The coloring composition according to <1>,

in which X in Formula (A) represents a substituent represented byFormula (X1), and R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (X1)satisfy the condition (i).

<3> The coloring composition according to <1>.

in which X in Formula (A) represents a substituent represented byFormula (X2), and R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ inFormula (X2) satisfy the condition (iii).

<4> The coloring composition according to <1>,

in which X in Formula (A) represents a substituent represented byFormula (X3), and R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ inFormula (X3) satisfy the condition (v).

<5> The coloring composition according to any one of <1> to <4>,

in which a total content of a content of the compound represented byFormula (1), a content of the compound represented by Formula (D), and acontent of the compound represented by Formula (E) is 2.0 to 5.0 mass %with respect to the coloring composition.

<6> The coloring composition according to any one of <1> to <5>,

in which in a case where the content of the compound represented byFormula (1) is represented by W₁, the content of the compoundrepresented by Formula (D) is represented by W_(D), and the content ofthe compound represented by Formula (E) is represented by W_(E), a massratio W₁/(W_(D)+W_(E)) is 90/10 to 60/40.

<7> An ink jet recording ink comprising the coloring compositionaccording to any one of <1> to <6>.

<8> An ink jet recording method using the ink jet recording inkaccording to <7>.

<9> An ink jet printer cartridge that is filled with the ink jetrecording ink according to <7>.

According to the present invention, it is possible to provide: acoloring composition with which an image having excellent color,saturation, and adhesion (printing density) and having excellent lightfastness, ozone fastness, and moisture resistance can be formed and thathas excellent jetting stability in an ink jet printer; an ink jetrecording ink including the coloring composition; an ink jet recordingmethod using the ink jet recording ink; and an ink jet printer cartridgethat is filled with the ink jet recording ink.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a diagram showing a ¹H-NMR (nuclear magnetic resonance)spectrum of an exemplary compound (1-11) in dimethyl sulfoxide-d6.

FIG. 2 is a diagram showing a ¹H-NMR spectrum of an exemplary compound(1-18) in dimethyl sulfoxide-d6.

FIG. 3 is a diagram showing a ¹H-NMR spectrum of an exemplary compound(1-26) in dimethyl sulfoxide-d6.

FIG. 4 is a diagram showing a ¹H-NMR spectrum of an exemplary compound(1-30) in dimethyl sulfoxide-d6.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

Hereinafter, the present invention will be described in detail.

First, specific examples of a substituent in the present invention aredefined as a substituent group A.

(Substituent Group A)

Examples of the substituent group A include a halogen atom, an alkylgroup, an aralkyl group, an alkenyl group, an alkynyl group, an arylgroup, a heterocyclic group, a cyano group, a hydroxyl group, a nitrogroup, an alkoxy group, an aryloxy group, a silyloxy group, aheterocyclic oxy group, an acyloxy group, a carbamoyloxy group, analkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group, anacylamino group, an aminocarbonylamino group, an alkoxycarbonylaminogroup, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl-or aryl-sulfonylamino group, a mercapto group, an alkylthio group, anarylthio group, a heterocyclic thio group, a sulfamoyl group, an alkyl-or aryl-sulfinyl group, an alkyl- or aryl-sulfonyl group, an acyl group,an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, anaryl or heterocyclic azo group, an imido group, a phosphino group, aphosphinyl group, a phosphinyloxy group, a phosphinylamino group, asilyl group, and an ionic hydrophilic group. These substituents mayfurther have a substituent, and examples of this substituent include agroup selected from the above-described substituent group A.

Examples of the halogen atom include a fluorine atom, a chlorine atom, abromine atom, and an iodine atom.

Examples of the alkyl group include a linear, branched, or cyclicsubstituted or unsubstituted alkyl group. In addition, a cycloalkylgroup, a bicycloalkyl group, a tricycloalkyl structure and the likehaving many ring structures are also included. Alkyl groups (forexample, an alkyl group in an alkoxy group or an alkylthio group) insubstituents described below are also included in the examples of theabove-described alkyl group.

As the alkyl group, an alkyl group having 1 to 30 carbon atoms ispreferable, and examples thereof include a methyl group, an ethyl group,an n-propyl group, an i-propyl group, a t-butyl group, an n-octyl group,an eicosyl group, a 2-chloroethyl group, a 2-cyanoethyl group, and a2-ethylhexyl group. As the cycloalkyl group, a substituted orunsubstituted cycloalkyl group having 3 to 30 carbon atoms ispreferable, and examples thereof include a cyclohexyl group, acyclopentyl group, and a 4-n-dodecylcyclohexyl group. As thebicycloalkyl group, a substituted or unsubstituted bicycloalkyl grouphaving 5 to 30 carbon atoms is preferable, that is, a monovalent groupobtained by removing one hydrogen atom from bicycloalkane having 5 to 30carbon atoms is preferable, and examples thereof include abicyclo[1,2,2]heptan-2-yl group and a bicyclo[2,2,2]octan-3-yl group.

Examples of the aralkyl group include a substituted or unsubstitutedaralkyl group. As the substituted or unsubstituted aralkyl group, anaralkyl group having 7 to 30 carbon atoms is preferable, and examplesthereof include a benzyl group and a 2-phenethyl group.

Examples of the alkenyl group include a linear, branched, or a cyclicsubstituted or unsubstituted alkenyl group. In addition, a cycloalkenylgroup and a bicycloalkenyl group are also included.

As the alkenyl group, a substituted or unsubstituted alkenyl grouphaving 2 to 30 carbon atoms is preferable, and examples thereof includea vinyl group, an allyl group, a prenyl group, a geranyl group, and anoleyl group. As the cycloalkenyl group, a substituted or unsubstitutedcycloalkenyl group having 3 to 30 carbon atoms is preferable, that is, amonovalent group obtained by removing one hydrogen atom from cycloalkenehaving 3 to 30 carbon atoms is preferable, and examples thereof includea 2-cyclopenten-1-yl group and a 2-cyclohexen-1-yl group. As thebicycloalkenyl group, a substituted or unsubstituted bicycloalkenylgroup can be used. A substituted or unsubstituted bicycloalkenyl grouphaving 5 to 30 carbon atoms is preferable, that is, a monovalent groupobtained by removing one hydrogen atom from bicycloalkene having onedouble bond is preferable, and examples thereof include abicyclo[2,2,1]hept-2-en-1-yl group and a bicyclo[2,2,2]oct-2-en-4-ylgroup.

As the alkynyl group, a substituted or unsubstituted alkynyl grouphaving 2 to 30 carbon atoms is preferable, and examples thereof includean ethynyl group, a propargyl group, and a trimethylsilylethynyl group.

As the aryl group, a substituted or unsubstituted aryl group having 6 to30 carbon atoms is preferable, and examples thereof include a phenylgroup, a p-tolyl group, a naphthyl group, an m-chlorophenyl group, ano-hexadecanoylaminophenyl group.

As the heterocyclic group, a monovalent group obtained by removing onehydrogen atom from a 5- or 6-membered substituted or unsubstitutedaromatic or nonaromatic heterocyclic compound is preferable, and a 5- or6-membered aromatic heterocyclic group having 3 to 30 carbon atoms ismore preferable, and examples thereof include a 2-furyl group, a2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.Examples of the nonaromatic heterocyclic group include a morpholinylgroup.

As the alkoxy group, a substituted or unsubstituted alkoxy group having1 to 30 carbon atoms is preferable, and examples thereof include amethoxy group, an ethoxy group, an isopropoxy group, a t-butoxy group,an n-octyloxy group, and a 2-methoxyethoxy group.

As the aryloxy group, a substituted or unsubstituted aryloxy grouphaving 6 to 30 carbon atoms is preferable, and examples thereof includea phenoxy group, a 2-methylphenoxy group, a 4-t-butylphenoxy group, a3-nitrophenoxy group, and a 2-tetradecanoylaminophenoxy group.

As the silyloxy group, a substituted or unsubstituted silyloxy grouphaving 0 to 20 carbon atoms is preferable, and examples thereof includea trimethylsilyloxy group and a diphenylmethylsilyloxy group.

As the heterocyclic oxy group, a substituted or unsubstitutedheterocyclic oxy group having 2 to 30 carbon atoms is preferable, andexamples thereof include a 1-phenyltetrazole-5-oxy group and a2-tetrahydropyranyloxy group.

As the acyloxy group, a formyloxy group, a substituted or unsubstitutedalkylcarbonyloxy group having 2 to 30 carbon atoms, or a substituted orunsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms ispreferable, and examples thereof include an acetyloxy group, apivaloyloxy group, a stearoyloxy group, a benzoyloxy group, and ap-methoxyphenylcarbonyloxy group.

As the carbamoyloxy group, a substituted or unsubstituted carbamoyloxygroup having 1 to 30 carbon atoms is preferable, and examples thereofinclude an N,N-dimethylcarbamoyloxy group, an N,N-diethylcarbamoyloxygroup, a morpholinocarbonyloxy group, an N,N-di-n-octylaminocarbonyloxygroup, and an N-n-octylcarbamoyloxy group.

As the alkoxycarbonyloxy group, a substituted or unsubstitutedalkoxycarbonyloxy group having 2 to 30 carbon atoms is preferable, andexamples thereof include a methoxycarbonyloxy group, anethoxycarbonyloxy group, a t-butoxycarbonyloxy group, and ann-octylcarbonyloxy group.

As the aryloxycarbonyloxy group, a substituted or unsubstitutedaryloxycarbonyloxy group having 7 to 30 carbon atoms is preferable, andexamples thereof include a phenoxycarbonyloxy group, ap-methoxyphenoxycarbonyloxy group, and ap-n-hexadecyloxyphenoxycarbonyloxy group.

Examples of the amino group include an alkylamino group, an arylaminogroup, and a heterocyclic amino group. As the amino group, an aminogroup, a substituted or unsubstituted alkylamino group having 1 to 30carbon atoms, a substituted or unsubstituted anilino group having 6 to30 carbon atoms is preferable, and examples thereof include amethylamino group, a dimethylamino group, an anilino group, anN-methyl-anilino group, a diphenylamino group, and a triazinylaminogroup.

As the acylamino group, a formylamino group, a substituted orunsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, or asubstituted or unsubstituted arylcarbonylamino group having 6 to 30carbon atoms is preferable, and examples thereof include an acetylaminogroup, a pivaloylamino group, a lauroylamino group, a benzoylaminogroup, and a 3,4,5-tri-n-octyloxyphenylcarbonylamino group.

As the aminocarbonylamino group, a substituted or unsubstitutedaminocarbonylamino group having 1 to 30 carbon atoms is preferable, andexamples thereof include a carbamoylamino group, anN,N-dimethylaminocarbonylamino group, an N,N-diethylaminocarbonylaminogroup, and a morpholinocarbonylamino group.

As the alkoxycarbonylamino group, a substituted or unsubstitutedalkoxycarbonylamino group having 2 to 30 carbon atoms is preferable, andexamples thereof include a methoxycarbonylamino group, anethoxycarbonylamino group, a t-butoxycarbonylamino group, ann-octadecyloxycarbonylamino group, and an N-methyl-methoxycarbonylaminogroup.

As the aryloxycarbonylamino group, a substituted or unsubstitutedaryloxycarbonylamino group having 7 to 30 carbon atoms is preferable,and examples thereof include a phenoxycarbonylamino group, ap-chlorophenoxycarbonylamino group, and anm-n-octyloxyphenoxycarbonylamino group.

As the sulfamoylamino group, a substituted or unsubstitutedsulfamoylamino group having 0 to 30 carbon atoms is preferable, andexamples thereof include a sulfamoylamino group, anN,N-dimethylaminosulfonylamino group, and an N-n-octylaminosulfonylaminogroup.

As the alkyl- or aryl-sulfonylamino group, a substituted orunsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms or asubstituted or unsubstituted arylsulfonylamino group having 6 to 30carbon atoms is preferable, and examples thereof include amethylsulfonylamino group, a butylsulfonylamino group, aphenylsulfonylamino group, a 2,3,5-trichlorophenylsulfonylamino group,and a p-methylphenylsulfonylamino group.

As the alkylthio group, a substituted or unsubstituted alkylthio grouphaving 1 to 30 carbon atoms is preferable, and examples thereof includea methylthio group, an ethylthio group, and an n-hexadecylthio group.

As the arylthio group, a substituted or unsubstituted arylthio grouphaving 6 to 30 carbon atoms is preferable, and examples thereof includea phenylthio group, a p-chlorophenylthio group, and anm-methoxyphenylthio group.

As the heterocyclic thio group, a substituted or unsubstitutedheterocyclic thio group having 2 to 30 carbon atoms is preferable, andexamples thereof include a 2-benzothiazolylthio group and a1-phenyltetrazole-5-ylthio group.

As the sulfamoyl group, a substituted or unsubstituted sulfamoyl grouphaving 0 to 30 carbon atoms is preferable, and examples thereof includean N-ethylsulfamoyl group, an N-(3-dodecyloxypropyl)sulfamoyl group, anN,N-dimethylsulfamoyl group, an N-acetylsulfamoyl group, anN-benzoylsulfamoyl group, and an N—(N′-phenylcarbamoyl)sulfamoyl group.

As the alkyl- or aryl-sulfinyl group, a substituted or unsubstitutedalkylsulfinyl group having 1 to 30 carbon atoms or a substituted orunsubstituted arylsulfinyl group having 6 to 30 carbon atoms ispreferable, and examples thereof include a methylsulfinyl group, anethylsulfinyl group, a phenylsulfinyl group, and ap-methylphenylsulfinyl group.

As the alkyl- or aryl-sulfonyl group, a substituted or unsubstitutedalkylsulfonyl group having 1 to 30 carbon atoms or a substituted orunsubstituted arylsulfonyl group having 6 to 30 carbon atoms ispreferable, and examples thereof include a methylsulfonyl group, anethylsulfonyl group, a phenylsulfonyl group, and ap-methylphenylsulfonyl group.

As the acyl group, a formyl group, a substituted or unsubstitutedalkylcarbonyl group having 2 to 30 carbon atoms, a substituted orunsubstituted arylcarbonyl group having 7 to 30 carbon atoms, or asubstituted or unsubstituted heterocyclic carbonyl group having 2 to 30carbon atoms and being bonded to a carbonyl group through a carbon atomis preferable, and examples thereof include an acetyl group, a pivaloylgroup, a 2-chloroacetyl group, a stearoyl group, a benzoyl group, ap-n-octyloxyphenylcarbonyl group, a 2-pyridylcarbonyl group, and a2-furylcarbonyl group.

As the aryloxycarbonyl group, a substituted or unsubstitutedaryloxycarbonyl group having 7 to 30 carbon atoms is preferable, andexamples thereof include a phenoxycarbonyl group, ano-chlorophenoxycarbonyl group, an m-nitrophenoxycarbonyl group, and ap-t-butylphenoxycarbonyl group.

As the alkoxycarbonyl group, a substituted or unsubstitutedalkoxycarbonyl group having 2 to 30 carbon atoms is preferable, andexamples thereof include a methoxycarbonyl group, an ethoxycarbonylgroup, a t-butoxycarbonyl group, and an n-octadecyloxycarbonyl group.

As the carbamoyl group, a substituted or unsubstituted carbamoyl grouphaving 1 to 30 carbon atoms is preferable, and examples thereof includea carbamoyl group, an N-methylcarbamoyl group, an N,N-dimethylcarbamoylgroup, an N,N-di-n-octylcarbamoyl group, and anN-(methylsulfonyl)carbamoyl group.

As the aryl- or heterocyclic azo group, a substituted or unsubstitutedaryl azo group having 6 to 30 carbon atoms or a substituted orunsubstituted heterocyclic azo group having 3 to 30 carbon atoms ispreferable, and examples thereof include a phenylazo group, ap-chlorophenylazo group, and a 5-ethylthio-1,3,4-thiadiazol-2-ylazogroup.

As the imido group, for example, an N-succinimido group or anN-phthalimido group is preferable.

As the phosphino group, a substituted or unsubstituted phosphino grouphaving 0 to 30 carbon atoms is preferable, and examples thereof includea dimethylphosphino group, a diphenylphosphino group, and amethylphenoxyphosphino group.

As the phosphinyl group, a substituted or unsubstituted phosphinyl grouphaving 0 to 30 carbon atoms is preferable, and examples thereof includea phosphinyl group, a dioctyloxyphosphinyl group, and adiethoxyphosphinyl group.

As the phosphinyloxy group, a substituted or unsubstituted phosphinyloxygroup having 0 to 30 carbon atoms is preferable, and examples thereofinclude a diphenoxyphosphinyloxy group and a dioctyloxyphosphinyloxygroup.

As the phosphinylamino group, a substituted or unsubstitutedphosphinylamino group having 0 to 30 carbon atoms is preferable, andexamples thereof include a dimethoxyphosphinylamino group and adimethylaminophosphinylamino group.

As the silyl group, a substituted or unsubstituted silyl group having 0to 30 carbon atoms is preferable, and examples thereof include atrimethylsilyl group, a t-butyldimethylsilyl group, and aphenyldimethylsilyl group.

Examples of the ionic hydrophilic group include a sulfo group, acarboxyl group, a thiocarboxyl group, a sulfino group, a phosphonogroup, a dihydroxyphosphino group, a quaternary ammonium group, and ahydroxyl group which is substituted with an s-triazine ring. Inparticular, a sulfo group, a carboxyl group, or a hydroxyl group whichis substituted with an s-triazine ring is preferable, and a sulfo groupor a carboxyl group is more preferable. In addition, the ionichydrophilic group may be a cation or an anion, and a state including acation or an anion is called a salt. In addition, the carboxyl group,the phosphono group, the sulfo group, or the hydroxyl group may be inthe form of a salt, and examples of a counter cation which forms a saltwith the carboxyl group, the phosphono group, or the sulfo group includean ammonium ion, an alkali metal ion (for example, a lithium ion, asodium ion, or a potassium ion), and an organic cation (for example, atetramethylammonium ion, a tetramethylguanidium ion, ortetramethylphosphonium). Among these, a lithium salt, a sodium salt, apotassium salt, or an ammonium salt is preferable, a sodium salt or amixed salt containing a sodium salt as a major component is morepreferable, and a sodium salt is most preferable.

In the present invention, in a case where a compound is a salt, the saltis dissociated and present in a water-soluble ink in the form of ions.

[Compound Represented by Formula (1)]

A compound represented by the following Formula (1) will be described.

In Formula (1), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group. R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ each independently represent a hydrogen atom or a substituent. R²,R³, R⁷, and R⁸ each independently represent a hydrogen atom, an alkylgroup, or a substituent represented by the following Formula (A), and atleast one of R², R³, R⁷, or R⁸ represents a substituent represented bythe following Formula (A).

In Formula (A), X represents a substituent represented by the followingFormula (X1), (X2), or (X3). * represents a direct bond to a benzenering.

In Formula (X1), R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ each independentlyrepresent a hydrogen atom or a substituent. R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, andR⁴⁰⁵ satisfy the following condition (i) or (ii). * represents a directbond to a sulfur atom.

Condition (i): at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵represents a hydroxyl group and at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴,and R⁴⁰⁵ represents a carboxyl group

Condition (ii): at least two of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵represent a carboxyl group

In Formula (X2), R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ eachindependently represent a hydrogen atom or a substituent. R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ satisfy the following condition (iii)or (iv). * represents a direct bond to a sulfur atom.

Condition (iii): at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, andR⁵⁰⁷ represents a hydroxyl group and at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³,R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ represents a carboxyl group

Condition (iv): at least two of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, andR⁵⁰⁷ represent a carboxyl group

In Formula (X3), R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ eachindependently represent a hydrogen atom or a substituent. R⁶⁰¹, R⁶⁰²,R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ satisfy the following condition (v) or(vi). * represents a direct bond to a sulfur atom.

Condition (v): at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, andR⁶⁰⁷ represents a hydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³,R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ represents a carboxyl group

Condition (vi): at least two of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, andR⁶⁰⁷ represent a carboxyl group

In Formula (1), R¹¹, R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ eachindependently represent a hydrogen atom or a substituent. In a casewhere R¹¹, R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰ represent asubstituent, the substituent is selected from, for example, thesubstituent group A.

It is preferable that R¹¹, R¹³, R¹⁴, R¹⁶, R¹⁷, R¹⁸, R¹⁹, and R²⁰represent a hydrogen atom.

In Formula (1), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group. From the viewpoint of raw material availability andsynthesis easiness, an alkyl group having 1 to 6 carbon atoms ispreferable, an alkyl group having 1 to 3 carbon atoms is morepreferable, and a methyl group or an ethyl group is still morepreferable. In addition, the alkyl group represented by R¹, R⁵, R⁶, andR¹⁰ may have a substituent, and this substituent is selected from, forexample, the substituent group A.

In Formula (1), R⁴, R⁹, R¹², and R¹⁵ each independently represent ahydrogen atom or a substituent. In a case where R⁴, R⁹, R¹², and R¹⁵represent a substituent, the substituent is preferably an alkyl group oran ionic hydrophilic group.

As the alkyl group, an alkyl group having 1 to 6 carbon atoms ispreferable, an alkyl group having 1 to 3 carbon atoms is morepreferable, a methyl group or an ethyl group is still more preferable,and a methyl group is even still more preferable.

As the ionic hydrophilic group, a carboxyl group, a sulfo group, or aphosphono group is preferable. Examples of a counter cation of the ionichydrophilic group include a hydrogen atom (proton), an alkali metalcation (a lithium ion, a sodium ion, or a potassium ion), and anammonium ion. From the viewpoint of synthesis easiness (easyhandleability of dye powder), the counter cation of the ionichydrophilic group is preferably an alkali metal cation.

It is preferable that at least one of R⁴, R⁹, R¹², or R¹⁵ represents anionic hydrophilic group, and it is more preferable that two or more ofR⁴, R⁹, R¹², or R¹⁵ represents an ionic hydrophilic group.

A case where R¹² and R¹⁵ represent an ionic hydrophilic group and R⁴ andR⁹ represent a hydrogen atom or a case where R⁴ and R⁹ represent anionic hydrophilic group and R¹² and R¹⁵ represent a hydrogen atom ispreferable, and a case where R¹² and R¹⁵ represent an ionic hydrophilicgroup and R⁴ and R⁹ represent a hydrogen atom is more preferable.

R⁴ and R⁹ each independently represent a hydrogen atom, a sulfo group,or a carboxyl group and preferably a hydrogen atom or a sulfo group.

R¹² and R¹⁵ each independently represent a hydrogen atom, a sulfo group,or a carboxyl group and preferably a hydrogen atom or a sulfo group.

In Formula (1), R², R³, R⁷, and R⁸ each independently represent ahydrogen atom, an alkyl group, or a substituent represented by Formula(A), and at least one of R², R³, R⁷, or R⁸ represents a substituentrepresented by Formula (A).

In a case where R², R³, R⁷, and R⁸ represent an alkyl group, an alkylgroup having 1 to 6 carbon atoms is preferable, an alkyl group having 1to 3 carbon atoms is more preferable, and a methyl group or an ethylgroup is still more preferable. In addition, the alkyl group representedby R², R³, R⁷, and R⁸ may have a substituent, and this substituent isselected from, for example, the substituent group A.

A case where R² and R⁷ each independently represent a substituentrepresented by Formula (A) and R³ and R⁸ each independently represent analkyl group or a case where R³ and R⁸ each independently represent asubstituent represented by Formula (A) and R² and R⁷ each independentlyrepresent an alkyl group is preferable, and a case where R² and R⁷ eachindependently represent a substituent represented by Formula (A) and R³and R⁸ each independently represent an alkyl group is more preferable.

In Formula (A), X represents a substituent represented by Formula (X1),(X2), or (X3).

Examples of a counter cation of the carboxyl group represented byFormula (X1), (X2), or (X3) include a hydrogen atom (proton), an alkalimetal cation (a lithium ion, a sodium ion, or a potassium ion), and anammonium ion. The counter cation of the carboxyl group is preferably analkali metal cation.

In Formula (X1), R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ each independentlyrepresent a hydrogen atom or a substituent. R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, andR⁴⁰⁵ satisfy the following condition (i) or (ii).

Condition (i): at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵represents a hydroxyl group and at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴,and R⁴⁰⁵ represents a carboxyl group

Condition (ii): at least two of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represent a carboxyl group

It is preferable that R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (X1)satisfy the condition (i). That is, it is preferable that at least oneof R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a hydroxyl group and atleast one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a carboxylgroup.

Among R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ the number of hydroxyl groups ispreferably 1 to 3, more preferably 1 or 2, and still more preferably 1.The number of carboxyl groups is more preferably 1 to 3 and still morepreferably 1 or 2.

A case where R¹⁰³ represents a hydroxyl group and R⁴⁰² represents acarboxyl group or a case where R⁴⁰¹ represents a hydroxyl group and R⁴⁰²represents a carboxyl group is preferable, and a case where R⁴⁰¹represents a hydroxyl group and R⁴⁰² represents a carboxyl group is morepreferable.

In a case where R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ represent asubstituent, the substituent is selected from, for example, thesubstituent group A. In particular, an alkyl group or an alkoxy group ispreferable, an alkyl group having 1 to 6 carbon atoms or an alkoxy groupis more preferable, an alkyl group having 1 to 3 carbon atoms or analkoxy group is still more preferable, and a methyl group or a methoxygroup is even still more preferable. In addition, in a case where R⁴⁰¹,R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ represent a substituent, examples of thesubstituent in an aspect different from the above-described aspectinclude a carboxyl group, a chlorine atom, a nitro group, and atrifluoromethyl group. Among these, a carboxyl group, a chlorine atom,or a nitro group is more preferable, and a carboxyl group is still morepreferable. In particular, in a case where R⁴⁰¹ represents a hydroxylgroup and R⁴⁰² represents a carboxyl group, it is preferable that R⁴⁰⁴represents the above-described substituent (a carboxyl group, a chlorineatom, a nitro group, or a trifluoromethyl group).

In a case where R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (X1) satisfythe condition (ii), it is preferable that R⁴⁰² and R⁴⁰⁴ represent acarboxyl group.

Specific examples of the group represented by Formula (X1) will be shownbelow, but the present invention is not limited to the examples. Instructural formulae of the following specific compounds, Me represents amethyl group. * represents a direct bond to a sulfur atom.

In Formula (X2), R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ eachindependently represent a hydrogen atom or a substituent. R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ satisfy the following condition (iii)or (iv).

Condition (iii): at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, andR⁵⁰⁷ represents a hydroxyl group and at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³,R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ represents a carboxyl group

Condition (iv): at least two of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, andR⁵⁰⁷ represent a carboxyl group

It is preferable that R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ inFormula (X2) satisfy the condition (iii). That is, it is preferable thatat least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷ represents ahydroxyl group and at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶,or R⁵⁰⁷ represents a carboxyl group.

In a case where R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ represent asubstituent, the substituent is selected from, for example, thesubstituent group A. In particular, an alkyl group or an alkoxy group ispreferable, an alkyl group having 1 to 6 carbon atoms or an alkoxy groupis more preferable, an alkyl group having 1 to 3 carbon atoms or analkoxy group is still more preferable, and a methyl group or a methoxygroup is even still more preferable.

Among R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷, the number ofhydroxyl groups is preferably 1 to 3, more preferably 1 or 2, and stillmore preferably 1. The number of carboxyl groups is more preferably 1 or2 and still more preferably 1.

A case where R⁵⁰⁴ represents a hydroxyl group and R⁵⁰³ represents acarboxyl group or a case where R⁵⁰⁴ represents a hydroxyl group and R⁵⁰⁵represents a carboxyl group is preferable, and a case where R⁵⁰⁴represents a hydroxyl group and R⁵⁰³ represents a carboxyl group is morepreferable.

Specific examples of the group represented by Formula (X2) will be shownbelow, but the present invention is not limited to the examples. *represents a direct bond to a sulfur atom.

In Formula (X3), R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ eachindependently represent a hydrogen atom or a substituent. R⁶⁰¹, R⁶⁰²,R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ satisfy the following condition (v) or(vi). * represents a direct bond to a sulfur atom.

Condition (v): at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, orR⁶⁰⁷ represents a hydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³,R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represents a carboxyl group

Condition (vi): at least two of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, orR⁶⁰⁷ represent a carboxyl group

It is preferable that R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ inFormula (X3) satisfy the condition (v). That is, it is preferable thatat least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represents ahydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,or R⁶⁰⁷ represents a carboxyl group.

In a case where R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ represent asubstituent, the substituent is selected from, for example, thesubstituent group A. In particular, an alkyl group or an alkoxy group ispreferable, an alkyl group having 1 to 6 carbon atoms or an alkoxy groupis more preferable, an alkyl group having 1 to 3 carbon atoms or analkoxy group is still more preferable, and a methyl group or a methoxygroup is even still more preferable.

Among R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷, the number ofhydroxyl groups is preferably 1 to 3, more preferably 1 or 2, and stillmore preferably 1. The number of carboxyl groups is more preferably 1 or2 and still more preferably 1.

A case where R⁶⁰⁶ represents a hydroxyl group and R⁶⁰⁵ represents acarboxyl group or a case where R⁶⁰³ represents a hydroxyl group and R⁶⁰²represents a carboxyl group is preferable, and a case where R⁶⁰⁶represents a hydroxyl group and R⁶⁰⁵ represents a carboxyl group is morepreferable.

Specific examples of the group represented by Formula (X3) will be shownbelow, but the present invention is not limited to the examples. *represents a direct bond to a sulfur atom.

It is preferable that the compound represented by Formula (1) is acompound represented by the following Formula (2), (3), or (4).

In Formula (2), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group. R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ each independently represent a hydrogen atom or a substituent. R³and R⁸ each independently represent a hydrogen atom or an alkyl group.R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ each independently represent a hydrogenatom or a substituent. R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ satisfy thefollowing condition (i-1) or (ii-1), R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, and R⁴¹⁰each independently represent a hydrogen atom or a substituent. R⁴⁰⁶,R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, and R⁴¹⁰ satisfy the following condition (i-2) or(ii-2).

Condition (i-1): at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represents a hydroxyl group and at least one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴,or R⁴⁰⁵ represents a carboxyl group

Condition (ii-1): at least two of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represent a carboxyl group

Condition (i-2): at least one of R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, or R⁴¹⁰represents a hydroxyl group and at least one of R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹,or R⁴¹⁰ represents a carboxyl group

Condition (ii-2): at least two of R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, or R⁴¹⁰represent a carboxyl group

In Formula (3), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group. R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ each independently represent a hydrogen atom or a substituent. R³and R⁸ each independently represent a hydrogen atom or an alkyl group.R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ each independentlyrepresent a hydrogen atom or a substituent. R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴,R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ satisfy the following condition (iii-1) or (iv-1).R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹, R⁵¹², R⁵¹³, and R⁵¹⁴ each independentlyrepresnet a hydrogen atom or a substituent. R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R¹¹⁰,R¹¹¹, R⁵¹², R⁵¹³, and R⁵¹⁴ satisfy the following condition (iii-2) or(iv-2).

Condition (iii-1): at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶,or R⁵⁰⁷ represents a hydroxyl group and at least one of R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷ represents a carboxyl group

Condition (iv-1): at least two of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, orR⁵⁰⁷ represent a carboxyl group

Condition (iii-2): at least one of R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹, R⁵¹², R⁵¹³,and R⁵¹⁴ represents a hydroxyl group and at least one of R⁵⁰⁸, R⁵⁰⁹,R⁵¹⁰, R⁵¹¹, R⁵¹², R⁵¹³, and R⁵¹⁴ represents a carboxyl group

Condition (iv-2): at least two of R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹, R⁵¹², R⁵¹³,and R⁵¹⁴ represent a carboxyl group

In Formula (4), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group. R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ each independently represent a hydrogen atom or a substituent. R³and R⁸ each independently represent a hydrogen atom or an alkyl group.R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ each independentlyrepresent a hydrogen atom or a substituent. R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴,R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ satisfy the following condition (v-1) or (vi-1),R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³, and R⁶¹⁴ each independentlyrepresent a hydrogen atom or a substituent. R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹,R⁶¹², R⁶¹³, and R⁶¹⁴ satisfy the following condition (v-2) or (vi-2).

Condition (v-1): at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, orR⁶⁰⁷ represents a hydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³,R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represents a carboxyl group

Condition (vi-1): at least two of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, orR⁶⁰⁷ represent a carboxyl group

Condition (v-2): at least one of R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³, orR⁶¹⁴ represents a hydroxyl group and at least one of R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰,R⁶¹¹, R⁶¹², R⁶¹³, or R⁶¹⁴ represents a carboxyl group

Condition (vi-2): at least two of R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³, orR⁶¹⁴ represent a carboxyl group

R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ in Formula (2) have the same definitions and the same preferableranges as R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷,R¹⁸, R¹⁹, and R²⁰ in Formula (1), respectively.

R³ and R⁸ in Formula (2) each independently represent a hydrogen atom oran alkyl group and preferably an alkyl group. As the alkyl group, analkyl group having 1 to 6 carbon atoms is preferable, an alkyl grouphaving 1 to 3 carbon atoms is more preferable, and a methyl group or anethyl group is still more preferable. In addition, the alkyl group mayhave a substituent, and this substituent is selected from, for example,the substituent group A.

It is preferable that R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (2)satisfy the condition (i-1). That is, it is preferable that at least oneof R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a hydroxyl group and atleast one of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a carboxylgroup. R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ have the same preferable rangesas R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (X1), respectively.

It is preferable that R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, and R⁴¹⁰ in Formula (2)satisfy the condition (i-2). That is, it is preferable that at least oneof R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, and R⁴¹⁰ represents a hydroxyl group and atleast one of R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, or R⁴¹⁰ represents a carboxylgroup. R⁴⁰⁶, R⁴⁰⁷, R⁴⁰⁸, R⁴⁰⁹, and R⁴¹⁰ have the same preferable rangesas R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (2), respectively.

R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹,and R²⁰ in Formula (3) have the same definitions and the same preferableranges as R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷,R¹⁸, R¹⁹, and R²⁰ in Formula (1), respectively.

R³ and R⁸ in Formula (3) each independently represent a hydrogen atom oran alkyl group and preferably an alkyl group. As the alkyl group, analkyl group having 1 to 6 carbon atoms is preferable, an alkyl grouphaving 1 to 3 carbon atoms is more preferable, and a methyl group or anethyl group is still more preferable. In addition, the alkyl group mayhave a substituent, and this substituent is selected from, for example,the substituent group A.

It is preferable that R⁵⁰⁶, R⁵⁰⁷, R⁵⁰⁸, R⁵⁰⁹, and R⁵¹⁰ in Formula (3)satisfy the condition (iii-1). That is, it is preferable that at leastone of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷ represents a hydroxylgroup and at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷represents a carboxyl group. R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷have the same preferable ranges as R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶,and R⁵⁰⁷ in Formula (X2), respectively.

It is preferable that R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R¹¹¹, R⁵¹², R⁵¹³, and R⁵¹⁴ inFormula (3) satisfy the condition (iii-2). That is, it is preferablethat at least one of R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹, R⁵¹², R⁵¹³, or R⁵¹⁴represents a hydroxyl group and at least one of R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹,R⁵¹², R⁵¹³, or R⁵¹⁴ represents a carboxyl group. R⁵⁰⁸, R⁵⁰⁹, R⁵¹⁰, R⁵¹¹,R⁵¹², R⁵¹³, and R⁵¹⁴ have the same preferable ranges as R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ in Formula (3), respectively.

R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹,and R²⁰ in Formula (4) have the same definitions and the same preferableranges as R¹, R⁴, R⁵, R⁶, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷,R¹⁸, R¹⁹, and R²⁰ in Formula (1), respectively.

R³ and R⁸ in Formula (4) each independently represent a hydrogen atom oran alkyl group and preferably an alkyl group. As the alkyl group, analkyl group having 1 to 6 carbon atoms is preferable, an alkyl grouphaving 1 to 3 carbon atoms is more preferable, and a methyl group or anethyl group is still more preferable. In addition, the alkyl group mayhave a substituent, and this substituent is selected from, for example,the substituent group A.

It is preferable that R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ inFormula (4) satisfy the condition (v-1). That is, it is preferable thatat least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represents ahydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,or R⁶⁰⁷ represents a carboxyl group. R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,and R⁶⁰⁷ have the same preferable ranges as R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴,R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ in Formula (X3), respectively.

It is preferable that R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³, and R⁶¹⁴ inFormula (4) satisfy the condition (v-2). That is, it is preferable thatat least one of R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³, or R⁶¹⁴ represents ahydroxyl group and at least one of R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³,or R⁶¹⁴ represents a carboxyl group. R⁶⁰⁸, R⁶⁰⁹, R⁶¹⁰, R⁶¹¹, R⁶¹², R⁶¹³,and R⁶¹⁴ have the same preferable ranges as R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴,R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ in Formula (4), respectively.

Hereinafter, specific examples of the compound represented by Formula(1) will be shown, but the present invention is not limited thereto. Inthe following specific structural formulae of the compounds, Merepresents a methyl group, and Et represents an ethyl group.

An exemplary specific synthesis method of the compound represented byFormula (1) will be described in Examples below.

[Compound represented by Formula (D)]

In Formula (D), R²¹ and R²² each independently represent a hydrogen atomor a substituted or unsubstituted alkyl group.

Y₂₁ and Y₂₂ each independently represent a chlorine atom, a hydroxylgroup, a substituted or unsubstituted amino group, an alkoxy group, asubstituted or unsubstituted phenoxy group, or a substituted orunsubstituted naphthyloxy group.

Xd represents a divalent linking group.

M⁴ represents a hydrogen atom or a counter cation. M⁴′s may be the sameas or different from each other.

In Formula (D), R₂₁ and R₂₂ each independently represent a hydrogen atomor a substituted or unsubstituted alkyl group.

In a case where R₂₁ and R₂₂ represent an alkyl group, the alkyl groupmay be linear, branched, or cyclic (cycloalkyl group) and is preferablyan alkyl group having 1 to 10 carbon atoms, more preferably an alkylgroup having 1 to 8 carbon atoms, still more preferably an alkyl grouphaving 1 to 6 carbon atoms, and even more preferably an alkyl grouphaving 1 to 4 carbon atoms.

In a case where the alkyl group is a cyclic alkyl group, a cyclohexylgroup is preferable.

As the alkyl group, a linear or branched alkyl group is more preferable.

Specific examples of the alkyl group include a methyl group, an ethylgroup, an n-propyl group, an isopropyl group, an n-butyl group, at-butyl group, an n-hexyl group, an n-octyl group, and a cyclohexylgroup.

In a case where R₂₁ and R₂₂ represent an alkyl group, the alkyl groupmay have a substituent. As the substituent, a hydroxyl group, a cyanogroup, or an amino group which is substituted with an alkyl group ispreferable.

In a case where the hydroxyl group or the cyano group is substituted, anethyl group is most preferable as the alkyl group.

Examples of the amino group which is substituted with an alkyl groupinclude a monoalkylamino group and a dialkylamino group. The alkyl groupis preferably linear or branched. A mono or dialkylamino group which issubstituted with an alkyl group having 1 to 8 carbon atoms ispreferable, a mono or dialkylamino group which is substituted with analkyl group having 1 to 6 carbon atoms is more preferable, a mono ordialkylamino group which is substituted with an alkyl group having 1 to4 carbon atoms is still more preferable, and a mono or dialkylaminogroup which is substituted with a methyl group or an ethyl group is evenstill more preferable.

From the viewpoint of raw material availability, R₂₁ and R₂₂ representpreferably a hydrogen atom or an unsubstituted alkyl group, morepreferably a hydrogen atom or a methyl group, and still more preferablya methyl group.

In Formula (D), Y₂₁ and Y₂₂ each independently represent a chlorineatom, a hydroxyl group, a substituted or unsubstituted amino group, analkoxy group, a substituted or unsubstituted phenoxy group, or asubstituted or unsubstituted naphthyloxy group.

In a case where Y₂₁ and Y₂₂ represent an amino group, the amino groupmay have a substituent. As the substituent, an alkyl group or an arylgroup is preferable.

In a case where Y₂₁ and Y₂₂ represent an amino group (alkylamino group)which has an alkyl group as a substituent, the amino group may be amonoalkylamino group or a dialkylamino group.

The alkyl group may be linear, branched, or cyclic (cycloalkyl group).

In a case where the alkyl group is a linear or branched alkyl group, analkyl group having 1 to 8 carbon atoms is preferable, and examplesthereof include a methyl group, an ethyl group, a butyl group, and a2-ethylhexyl group.

In a case where the alkyl group is a linear or branched alkyl group, thealkyl group may further have a substituent. As the substituent, analkylamino group, an aryl group, a sulfo group, a carboxyl group, or ahydroxyl group is preferable. In a case where the alkyl group furtherhas a substituent, it is preferable that the alkyl group is an alkylgroup having a substituent selected from the group consisting of a sulfogroup, a carboxyl group, and a hydroxyl group, an alkyl group (aralkylgroup) having an aryl group, or an alkyl group having an alkylaminogroup.

As the alkyl group having a substituent selected from the groupconsisting of a sulfo group, a carboxyl group, and a hydroxyl group, analkyl group having 1 to 4 carbon atoms is preferable, and examplesthereof include a methyl group, an ethyl group, an n-propyl group, andan n-butyl group.

Specific examples of the mono or dialkylamino group having a sulfo groupor a carboxyl group include a 2-sulfoethylamino group, acarboxymethylamino group, a 2-carboxyethylamino group, a1-carboxyethylamino group, a 1,2-dicarboxyethylamino group, and adi(carboxymethyl)amino group.

Specific examples of the mono or dialkylamino group having a hydroxylgroup include a hydroxyethylamino group and a dihydroxyethylamino group.

As the amino group having an aralkyl group, an amino group having analkyl group having 1 to 6 carbon atoms which is substituted with aphenyl group is preferable, and examples thereof include a benzylaminogroup, a phenethylamino group, and a phenylpropylamino group.

The alkylamino group as the substituent may be a monoalkylamino group ora dialkylamino group, and has the same specific examples and the samepreferable ranges as the alkylamino group represented by Y₂₁ and Y₂₂.

In a case where Y₂₁ and Y₂₂ represent an amino group having a cycloalkylgroup, the cycloalkyl group is preferably a cycloalkyl group having 5 to7 carbon atoms, and examples thereof include a cyclohexyl group and acyclopentyl group.

In a case where Y₂₁ and Y₂₂ represent an amino group (arylamino group)having an aryl group as a substituent, an amino group which issubstituted with a phenyl group or a naphthyl group is preferable.

As the amino group which is substituted with a phenyl group, an anilinogroup is preferable. The anilino group may be an unsubstituted anilinogroup or an anilino group in which at least one substituent selectedfrom the group consisting of a sulfo group and a carboxyl group on abenzene ring is further substituted, and examples thereof include a2,5-disulfoanilino group, a 3-sulfoanilino group, a 2-sulfoanilinogroup, a 4-sulfoanilino group, a 2-carboxy-4-sulfoanilino group, a2-carboxy-5-sulfoanilino group.

The amino group (naphthylamino group) which is substituted with anaphthyl group may be an unsubstituted naphthylamino group or anaphthylamino group in which a naphthyl group is further substitutedwith a sulfo group, and examples thereof include a3,6,8-trisulfo-1-naphthylamino group, a 4,6,8-trisulfo-2-naphthylaminogroup, a 3,6,8-trisulfo-2-naphthylamino group and a4,8-disulfo-2-naphthylamino group.

In a case where Y₂₁ and Y₂₂ represent an alkoxy group, as the alkoxygroup, for example, an alkoxy group having 1 to 4 carbon atoms such as amethoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group,or a butoxy group is preferable.

In a case where Y₂₁ and Y₂₂ represent a phenoxy group, the phenoxy groupmay be an unsubstituted phenoxy group or a phenoxy group having asubstituent. As the substituent, at least one substituent selected fromthe group consisting of a sulfo group, a carboxy group, an acetylaminogroup, an amino group, and a hydroxyl group is preferable. Examples ofthe phenoxy group which is substituted with at least one substituentselected from the group consisting of a sulfo group, a carboxy group, anacetylamino group, an amino group, and a hydroxyl group include a4-sulfophenoxy group, a 4-carboxyphenoxy group, a 4-acetylamino-phenoxygroup, a 4-aminophenoxy group, a 4-hydroxyphenoxy group, and a3,5-di-carboxyphenoxy group.

In a case where Y₂₁ and Y₂₂ represent a naphthyloxy group, thenaphthyloxy group may be an unsubstituted naphthyloxy group or anaphthyloxy group having a substituent. As the substituent, at least onesubstituent selected from the group consisting of a sulfo group, acarboxy group, an acetylamino group, an amino group, and a hydroxylgroup is preferable. Examples of the naphthyloxy group which issubstituted with at least one substituent selected from the groupconsisting of a sulfo group, a carboxy group, an acetylamino group, anamino group, and a hydroxyl group include a 6-carboxy-2-naphthyloxygroup.

From the viewpoint of moisture resistance, Y₂₁ and Y₂₂ representpreferably a chlorine atom, a hydroxyl group, an unsubstituted aminogroup, a substituted amino group, a substituted or unsubstituted phenoxygroup, or a substituted or unsubstituted naphthyloxy group, morepreferably a phenoxy group having a substituent or a naphthyloxy grouphaving a substituent, and most preferably a phenoxy group having acarboxy group or a naphthyloxy group having a carboxy group.

In Formula (D), Xd represents a divalent linking group. As the divalentlinking group, for example, a divalent group in which a nitrogen atom oran oxygen atom is present at opposite terminals of a hydrocarbon residuehaving 1 to 20 carbon atoms which may include a nitrogen atom, an oxygenatom, or a sulfur atom and in which the nitrogen atom or the oxygen atomat the opposite terminals is a direct bond can be used, specificexamples thereof include a group represented by the following formula:—N(H)_(m)(-A-)_(n)N(H)_(m)—; or—O-A-O—.

(In the formulae, A represents a divalent hydrocarbon residue having 1to 20 carbon atoms which may include a nitrogen atom, an oxygen atom, ora sulfur atom, n represents 1 or 2, m represents 1 or 0, in a case wheren represents 1, m represents 1, and in a case where n represents 2, mrepresents 0).

Examples of the divalent hydrocarbon residue having 1 to 20 carbon atomswhich is represented by A include: a divalent aliphatic group having 1to 15 carbon atoms which may include one or two hetero atoms (forexample, a nitrogen atom, an oxygen atom or a sulfur atom), a divalentaromatic group having 3 to 10 carbon atoms (preferably 5 to 10 carbonatoms) which may include 1 to 3 hetero atoms (for example, a nitrogenatom, an oxygen atom, or a sulfur atom), and a divalent group which isformed by the aliphatic group and the aromatic group being bonded toeach other. These groups may have a substituent (in the case of a sulfogroup, a carboxyl group, an amino group, or an aromatic group, forexample, an alkyl group having 1 to 10 carbon atoms).

Examples of the aliphatic group include: a (poly)methylene having 1 to 6carbon atoms which may be substituted with an alkyl group having 1 to 10carbon atoms such as methylene, dimethylene(ethylene),trimethylene(propylene), 2-methyltrimethylene(2-methylpropylene),tetramethylene(butylene), or hexamethylene; a cycloalkylene having 5 to7 carbon atoms such as cyclopentane-1,2-diyl, cyclopentane-1,3-diyl,cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, orcycloheptane-diyl; an aliphatic group which includes an alkylene having1 to 10 carbon atoms and an aliphatic group having 5 to 7 carbon atoms(which may substituted with an alkylene having 1 to 10 carbon atoms)such as methylenecyclohexane-1,4-diylmethylene (—CH₂—C₆H₁₀—CH₂—),methylenedicyclohexane-diyl (—C₆H₁₀—CH₂—C₆H₁₀—),methylenebis(methylcyclohexane-diyl) {—C₆H₁₀(CH₃)—CH₂—C₆H₁₀(CH₃)—}, orcyclohexane-diyl-dimethylene (—CH₂—C₆H₁₀—CH₂—); and an aliphatic grouphaving 1 to 7 carbon atoms which includes a hetero atom such asmethyleneoxymethylene (—CH₂—O—CH₂—), bis(dimethylene)amino(—C₂H₄—NH—C₂H₄—), methylenethiomethylene (—CH₂—S—CH₂—), oroxydicyclohexane-diyl (—C₆H₁₀—O—C₆H₁₀—).

Examples of the divalent aromatic group include an aromatic group having6 to 10 carbon atoms such as phenylene (—C₆H₄—) or naphthylene(—C₁₀H₆—).

Examples of the divalent group which is formed by the aliphatic groupand the aromatic group being bonded to each other include xylylene(—CH₂—C₆H₄—CH₂—).

For example, it is more preferable that A represents dimethylene,hexamethylene, 1,3-xylylene, methylenedicyclohexane-4,1-diyl,methylenebis(2-methylcyclohexane-4,1-diyl), orcyclohexane-1,3-diyl-dimethylene.

Examples of the divalent linking group represented by Xd include: adiaminoalkylene group such as a 1,2-diaminoethylene group(—NH—CH₂CH₂—NH—), a 1,4-diaminobutylene group (—NH—C₄H₈—NH—), or a1,6-diaminohexylene group (—NH—C₆H₁₂—NH—); a diaminophenylene group suchas a 1,4-piperazinediyl group (—NC₄H₈N—), a 1,4-diaminophenylene group(—NH—C₆H₄-p-NH—), or a 1,3-diaminophenylene group (—NH—C₆H₄-m-NH—); asubstituted diaminophenylene group such as a4-sulfo-1,3-diaminophenylene group {—NH—C₆H₄(p-SO₃H)-m-NH-} or a5-carboxy-1,3-diaminophenylene group; a dioxy-substituted alkylene groupsuch as a 1,3-diaminoxylylene group (—NH—CH₂—C₆H₄-m-CH₂—NH—), a1,4-diaminoxylylene group (—NH—CH₂—C₆H₄-p-CH₂—NH—), a4,4′-diamino-2-sulfo-diphenylamino group{—NH—C₆H₄(m-SO₃H)—NH—C₆H₄-p-NH—}, a 4,4′-diaminodicyclohexylmethanegroup (—NH—C₆H₁₀-4-CH₂—C₆H₁₀-4′-NH—), a4,4′-diamino-3,3′-dimethyldicyclohexylmethane group{—NH—C₆H₁₀(3-CH₃)-4-CH₂—C₆H₁₀(3′-CH₃)-4′NH—), a1,3-bis(aminomethyl)cyclohexane group (—NH—CH₂—C₆H₁₀-3-CH₂—NH—), adioxyethylene group (—O—CH₂CH₂—O—), a 1,4-dioxybutylene group(—O—C₄H₈—O—), or a 2,2′-dioxyethylether group (—O—CH₂CH₂—O—CH₂CH₂—O—); a1,4-dioxyphenylene group (—O—C₆H₄-p-O—); a 1,3-dioxyphenylene group(—O—C₆H₄-m-O—); a 4,4′-dioxydiphenylether group (—O—C₆H₄-p-O—C₆H₄-p-O—);a 4,4′-dioxyphenylenethioether group (—O—C₆H₄-p-S—C₆H₄-p-O—); a 2,5- or2,6-norbomanediamino group; and a 1,4-dioxymethylcyclohexylene group(—O—CH₂—C₆H₁₀-4-CH₂—O—).

Examples of the group represented by the formula—N(H)_(m)(-A-)_(n)N(H)_(m)— in which n represents 2 and m represents 0include the 1,4-piperazinediyl group (—NC₄H₈N—).

It is preferable that Xd represents a diaminoethylene group, a1,4-piperazinediyl group, a 1,3-diaminoxylylene group, a4,4′-diaminodicyclohexylmethane group, a4,4′-diamino-3,3′-dimethyldicyclohexylmethane group, or a1,3-bis(aminomethyl)cyclohexane group.

In Formula (D), M⁴ represents a hydrogen atom or a counter cation. M⁴′smay be the same as or different from each other.

In a case where M⁴ in Formula (D) represents a hydrogen atom, thehydrogen atom is in the form of a free acid. In a case where M⁴ inFormula (D) represents a counter cation, the counter cation is in theform of a salt.

Examples of the counter cation which forms a salt include a monovalentcounter cation. For example, an alkali metal ion, an ammonium ion, or anorganic cation is preferable.

Examples of the organic cation include a cation in which a hydrogen ionis added to alkylamine or alkanolamine. Examples of the alkylamineinclude trimethylamine and triethylamine. Examples of the alkanolamineinclude monoethanolamine, diethanolamine, triethanolamine,monoisopropanolamine, diisopropanolamine, and triisopropanolamine.

From the viewpoint of solubility, an alkali metal ion is preferable, anda lithium ion, a sodium ion, or a potassium ion is more preferable. Inparticular, a sodium ion is preferable from the viewpoint of easymanufacturing.

In Formula (D), M⁴′s may be the same as or different from each other.That is, the compound represented by Formula (D) being in the form of asalt represent not only a case where all the sulfo groups are salts butalso a case where some sulfo groups are in the form of a free acid andsome sulfo groups are salts. In addition, as the counter cation whichforms a salt, one kind may be used alone, or a plurality of kinds may beused.

In addition, groups (for example, a carboxyl group) other than a sulfogroup which may form a salt are as described above.

Specific examples of the anthrapyridone compound represented by Formula(D) are shown in the following tables. In the following tables,“diaminoethylene” represents a 1,2-diaminoethylene group(—NH—CH₂CH₂—NH—). In addition, “Ph” represents a phenyl group.

For example, “PhO” represents a phenoxy group, “NHPh” represents ananilino group, and the same shall be applied to other groups. Inaddition, “NHPh(p-SO3H)” represents a 4-sulfoanilino group (“p-SO3H”represents that a sulfonate group is present at the para position of aphenyl group), “NHPh(COOH)2(3,5)” represents a 3,5-dicarboxyanilinogroup {“Ph(COOH)2(3,5)” represents that a carboxyl group is substitutedat the 3-position and the 5-position of a phenyl group}, and the sameshall be applied to other groups. In addition, “naphthyl” represents anaphthyl group, NH-2naphthyl(SO3H)3(3,6,8) represents3,6,8-trisulfo-2naphthylamino, and “NH(cyclohexyl)” representscyclohexylamino. In the following specific examples, a sulfo group and acarboxyl group may be in the form of a salt. In addition, although notdescribed in the tables, M⁴ represents a hydrogen atom or a countercation.

TABLE 1 No. R₂₁, R₂₂ Xd Y₂₁, Y₂₂ 2-0-1 CH3 diaminoethylene OH 2-0-2 CH3diaminoethylene Cl 2-0-3 CH3 diaminoethylene NH2 2-0-4 CH31,4-piperazinediyl Cl 2-0-5 CH3 1,4-piperazinediyl NH2 2-0-6 CH31,3-diaminoxylylene Cl 2-0-7 CH3 1,3-diaminoxylylene NH2 2-0-8 CH31,4-diaminoxylylene NH2 2-0-9 CH3 bis(3-aminopropyl)ether NH2 2-0-10 CH33,3′-iminodi(propylamine) NH2 2-0-11 CH3 2,2′-iminodi(ethylamine) NH22-0-12 CH3 1,4′-diaminobutylene NH2 2-0-13 CH3 1,6-diaminohexylene NH22-0-14 CH3 1,4-diaminophenylene NH2 2-0-15 CH3 1,3-diaminophenylene NH22-0-16 CH3 1,3-diamino-4-sulfophenylene NH2 2-0-17 CH31,3-diamino-5-carboxyphenylene NH2 2-0-18 CH34,4′-diamino-2-sulfodiphenyleamine NH2

TABLE 2 No. R₂₁, R₂₂ Xd Y₂₁, Y₂₂ 2-0-19 CH3 4,4′-diamino-3,3′- NH2dimethyl-dicyclohexylmethane 2-0-20 CH3 4,4′-diamino- NH2dicyclohexylmethane 2-0-21 CH3 diaminoethylene NHCCH2COOH) 2-0-22 CH3diaminoethylene NH(CH2CH2COOH) 2-0-23 CH3 diaminoethyleneNH(CH2(COOH)CH2COOH) 2-0-24 CH3 diaminoethylene NH(CH2(COOH)CH2CH2COOH)2-0-25 CH3 diaminoethylene CH3O 2-0-26 CH3 diaminoethylene C6H5O 2-0-27CH3 diaminoethylene NH(CH2CH2SO3H) 2-0-28 CH3 diaminoethylene NHC6H52-0-29 CH3 diaminoethylene NHPh(p-SO3H) 2-0-30 CH3 diaminoethyleneNHPh(COOH)2(3,5) 2-0-31 CH3 diaminoethylene NHPh(COOH)2(2,5) 2-0-32 CH3diaminoethylene NHPh(o-SO3H) 2-0-33 CH3 diaminoethylene NHPh(m-SO3H)2-0-34 CH3 diaminoethylene NHPh(SO3H)2(2,5) 2-0-35 CH3 diaminoethyleneNH(CH2CH2CH2N(C2H5)2) 2-0-36 CH3 diaminoethylene NH(CH2CH2CH2N(CH3)2)2-0-37 CH3 diaminoethylene NH-2aphthyl(SO3H)3(3,6,8)

TABLE 3 No. R₂₁, R₂₂ Xd Y₂₁, R₂₂ 2-0-38 CH3 diaminoethyleneNH-2naphthyl(SO3H)3(4,6,8) 2-0-39 CH3 diaminoethyleneNH-2naphthyl(SO3H)2(4,8) 2-0-40 CH3 diaminoethylene NH(n-C4H9) 2-0-41CH3 diaminoethylene NH(cyclohexyl) 2-0-42 CH3 diaminoethyleneNH(CH2CH2OH) 2-0-43 CH3 diaminoethylene N(CH2CH2OH) 2-0-44 CH3diaminoethylene NHCH2Ph 2-0-45 H diaminoethylene NH2 2-0-46 H1,3-diaminoxylene NH2 2-0-47 H 1,4-piperazinediyl NH2 2-0-48 C2H51,3-diaminoxylene NH2 2-0-49 C4H9 1,3-diaminoxylene NH2 2-0-50 isoC3H71,3-diaminoxylene NH2 2-0-51 cyclohexyl 1,3-diaminoxylene NH2 2-0-52C3H6N(C2H5)2 1,3-diaminophenylene NH2 2-0-53 CH3 1,4-oxyphenylene NH22-0-54 CH3 4,4′-dioxydiphenylether NH2 2-0-55 CH34,4′-dioxydiphenylthioether NH2 2-0-56 CH3 4,4′-dioxydiphenylsulfone NH22-0-57 CH3 4,4′-dioxydiphenylmethane NH2 2-0-58 CH3 2,5- or2,6-norbornanediamino NH2 2-0-59 CH3 1,4-dioxymethylcyclohexylene NH22-0-60 CH3 2,5-dimehyl-1,4-piperazinediyl NH2

As the compound represented by Formula (D), the following compounds arealso preferable.

The compound represented by Formula (D) can be synthesized using awell-known synthesis method of the related art (for example, a synthesismethod described in JP2013-133396A).

[Compound Represented by Formula (E)]

In Formula (E), R₃₁ represents a hydrogen atom or a substituted orunsubstituted alkyl group.

Y₃₁ represents a chlorine atom, a hydroxyl group, a substituted orunsubstituted amino group, or a morpholino group.

M⁵ represents a hydrogen atom or a counter cation. M⁵′s may be the sameas or different from each other.

X₃₁ represents a group represented by the following Formula (E-1).

In Formula (E-1), R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ each independentlyrepresent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or—COOM′ (M′ represents a hydrogen atom or a counter cation). At least oneof R₃₂, R₃₃, R₃₄, R₃₅, or R₃₆ represents an alkyl group having 1 to 8carbon atoms or —COOM′. * represents a direct bond to a carbon atom.

In Formula (E), R₃₁ represents a hydrogen atom or a substituted orunsubstituted alkyl group.

In a case where R₃₁ represents an alkyl group, the alkyl group may havea substituent. The alkyl group, the specific examples of thesubstituent, and preferable ranges are the same as those describedregarding R₂₁ in Formula (D).

From the viewpoint of raw material availability, R₃₁ representspreferably a hydrogen atom or an unsubstituted alkyl group, morepreferably a hydrogen atom or a methyl group, and still more preferablya methyl group.

In Formula (E), Y₃₁ represents a chlorine atom, a hydroxyl group, asubstituted or unsubstituted amino group, or a morpholino group.

In a case where Y₃₁ represents an amino group, the amino group may havea substituent.

The amino group, the specific examples of the substituent, andpreferable ranges are the same as those described regarding Y₂₁ inFormula (D).

As Y₃₁, from the viewpoint of moisture resistance, a chlorine atom, ahydroxyl group, or an amino group is preferable, a hydroxyl group or anamino group is more preferable, and a hydroxyl group is still morepreferable.

In Formula (E), X₃₁ represents a group (substituted anilino group)represented by Formula (E-1).

In Formula (E-1), in a case where R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ representan alkyl group having 1 to 8 carbon atoms, as the alkyl group having 1to 8 carbon atoms, a linear or branched alkyl group is preferable, andexamples thereof include a methyl group, an ethyl group, an n-propylgroup, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexylgroup, and an n-octyl group.

In the case of the alkyl group, in consideration of color, it ispreferable that at least one of R₃₂ or R₃₆ represents an alkyl group andthe other one of R₃₂ or R₃₆ represents a hydrogen atom. In addition, asthe alkyl group, a methyl group, an ethyl group, an n-propyl group, oran isopropyl group is preferable.

M′ represents a hydrogen atom or a counter cation. Examples of thecounter cation include a monovalent counter cation. For example, analkali metal ion (preferably a lithium ion, a sodium ion, or a potassiumion, and more preferably a sodium ion), an ammonium ion, or an organiccation is preferable. Examples of the organic cation include a cation inwhich a hydrogen ion is added to alkylamine or alkanolamine. Examples ofthe alkylamine include trimethylamine and triethylamine. Examples of thealkanolamine include monoethanolamine, diethanolamine, triethanolamine,monoisopropanolamine, diisopropanolamine, and triisopropanolamine.

It is preferable that M′ represents a hydrogen atom or an alkali metalion.

As R₃₂ to R₃₆, an alkyl group having 1 to 8 carbon atoms or —COOM′ ispreferable, and it is preferable that, among R₃₂ to R₃₆, one to three(preferably one or two) represent an alkyl group having 1 to 8 carbonatoms or —COOM′ and the other groups represent a hydrogen atom.

In a case where two of R₃₂ to R₃₆ represent a group other than ahydrogen atom, it is preferable that R₃₂ and R₃₆, or R₃₃ and R₃₅represent a group other than a hydrogen atom. In a case where three ofR₃₂ to R₃₆ represent a group other than a hydrogen atom, it ispreferable that R₃₂, R₃₄, and R₃₆ represent a group other than ahydrogen atom. It is more preferable that, among R₃₂ to R₃₆, one tothree represent —COOM′ and the other groups represent a hydrogen atom.It is still more preferable that at least one of R₃₂, R₃₃, or R₃₅represent —COOM′.

Specific examples of X₃₁ include a 2-methylanilino group, a2,6-dimethylanilino group, a 2,5-dimethylanilino group, a2,4,6-trimethylanilino group, a 2,6-diethylanilino group, a2,5-diethylanilino group, a 2,6-di-iso-propylanilino group, a2,5-di-iso-propylanilino group, a 2-carboxyanilino group, a3-carboxyanilino group, a 4-carboxyanilino group, a 2,5-dicarboxyanilinogroup, a 3,5-dicarboxyanilino group, a 5-carboxy-2-methylanilino group,and a 5-carboxy-2-ethylanilino group.

X₃₁ represents preferably a 2,6-dimethylanilino group, a2,4,6-trimethylanilino group, a 2,6-diethylanilino group, a2,6-di-iso-propylanilino group, a 2-carboxyanilino group, or a3,5-dicarboxyanilino group, more preferably a 2,6-dimethylanilino group,a 2,6-diethylanilino group, a 2,6-di-iso-propylanilino group, a2-carboxyanilino group, or a 3,5-dicarboxyanilino group, and still morepreferably a 2-carboxyanilino group or a 3,5-dicarboxyanilino group.

In Formula (E), M⁵ represents a hydrogen atom or a counter cation. M⁵′smay be the same as or different from each other.

In a case where M⁵ in Formula (E) represents a hydrogen atom, thehydrogen atom is in the form of a free acid. In a case where M⁵ inFormula (E) represents a counter cation, the counter cation is in theform of a salt.

Examples of the counter cation which forms a salt include a monovalentcounter cation. For example, an alkali metal ion, an ammonium ion, or anorganic cation is preferable.

Examples of the organic cation include a cation in which a hydrogen ionis added to alkylamine or alkanolamine. Examples of the alkylamineinclude trimethylamine and triethylamine. Examples of the alkanolamineinclude monoethanolamine, diethanolamine, triethanolamine,monoisopropanolamine, diisopropanolamine, and triisopropanolamine.

From the viewpoint of water solubility, an alkali metal ion ispreferable, and a lithium ion, a sodium ion, or a potassium ion is morepreferable. In particular, a sodium ion is preferable from the viewpointof easy manufacturing.

In Formula (E), M⁵′s may be the same as or different from each other.That is, the compound represented by Formula (E) being in the form of asalt represent not only a case where all the sulfo groups are salts butalso a case where some sulfo groups are in the form of a free acid andsome sulfo groups are salts. In addition, as the counter cation whichforms a salt, one kind may be used alone, or a plurality of kinds may beused.

In addition, groups (for example, a carboxyl group) other than a sulfogroup which may form a salt are as described above.

Specific examples of the anthrapyridone compound represented by Formula(E) are shown in the following tables. In the following tables, (K)represents “carboxy”, and 2(K) represents “dicarboxy”. In the followingspecific examples, a carboxyl group may be in the form of a salt. Inaddition, although not described in the tables, M⁵ represents a hydrogenatom or a counter cation.

TABLE 4 No. R₃₁ X₃₁ Y₃₁ 3-0-1 CH3 2,6-dimethylanilino OH 3-0-2 CH32,6-dimethylanilino NH2 3-0-3 CH3 2,5-dimethylanilino OH 3-0-4 CH32-methylanilino OH 3-0-5 CH3 2,4,6-trimethylanilino OH 3-0-6 CH32,4,6-trimethylanilino NH2 3-0-7 H 2,4,6-trimethylanilino Cl 3-0-8 CH32,4,6-trimethylanilino 2-ethylhexylamino 3-0-9 CH32,6-diisopropylanilino OH 3-0-10 CH3 2,6-diisopropylanilino NH2 3-0-11C2H5 2,6-diisopropylanilino Cl 3-0-12 CH3 2,6-diisopropylanilinomonoethanolamino 3-0-13 CH3 2,5-diisopropylanilino OH 3-0-14 CH32,6-diethylanilino OH 3-0-15 CH3 2,6-diethylanilino NH2 3-0-16 CH32,6-diethylanilino Cl 3-0-17 CH3 2,6-diethylanilino 2-ethylhexylamino3-0-18 CH3 2,6-diethylanilino monoethanolamino 3-0-19 CH32,6-diethylanilino diethanolamino 3-0-20 C2H4OH 2,6-diethylanilinomorpholino 3-0-21 CH3 2,5-diethylanilino OH 3-0-22 CH32,5-diethylanilino NH2 3-0-23 CH3 2-(K)-anilino OH 3-0-24 CH32-(K)-anilino NH2 3-0-25 CH3 2,5-2(K)-anilino OH 3-0-26 C4H92,5-2(K)-anilino NH2 3-0-27 CH3 3,5-2(K)-anilino OH 3-0-28 CH33-(K)-anilino OH 3-0-29 CH3 4-(K)-anilino OH 3-0-30 CH35-N-2-methylanilino OH 3-0-31 CH3 5-(K)-2-ethylanilino OH 3-0-32 CH32,5-diisopropylanilino Cl 3-0-33 CH3 2,4,6-trimethylanilino Cl 3-0-34CH3 2-(K)-anilino Cl 3-0-35 CH3 3,5-2(K)-anilino Cl 3-0-36 CH34-(K)-anilino Cl 3-0-37 CH3 3-(K)-anilino Cl

The compound represented by Formula (E) can be synthesized using awell-known synthesis method of the related art (for example, a synthesismethod described in JP2013-133396A).

[Coloring Composition]

A coloring composition according to the present invention includes: thecompound represented by Formula (1), and at least one compound selectedfrom the group consisting of the compound represented by Formula (D) andthe compound represented by Formula (E).

As the compound represented by Formula (1) included in the coloringcomposition according to the present invention, one kind may be used, ora combination of two or more kinds may be used. In addition, as thecompound selected from the group consisting of the compound representedby Formula (D) and the compound represented by Formula (E) included inthe coloring composition according to the present invention, one kindmay be used, or a combination of two or more kinds may be used.

The coloring composition according to the present invention may furtherinclude a medium and, in a case where a solvent is used as the medium,is suitable as an ink jet recording ink. The coloring compositionaccording to the present invention can be prepared by using a lipophilicmedium or an aqueous medium as the medium and dissolving and/ordispersing the compound represented by Formula (1) therein. It ispreferable that an aqueous medium is used as the medium. Examples of thecoloring composition according to the present invention includes an inkcomposition excluding a medium.

The content (W₁) of the compound represented by Formula (1) in thecoloring composition is determined based on, for example, the kind ofthe compound represented by Formula (1), and the kind of the solventcomponent used for manufacturing the coloring composition. The content(W₁) of the compound represented by Formula (1) in the coloringcomposition is preferably 1.5 to 20.0 mass %, more preferably 1.5 to10.0 mass %, still more preferably 1.5 to 5.0 mass %, even still morepreferably 2.0 to 5.0 mass %, and most preferably 2.5 mass % or higherand lower than 5.0 mass % with respect to the total mass of the coloringcomposition.

The sum (W_(D)+W_(E)) of the content (W_(D)) of the compound representedby Formula (D) and the content (W_(E)) of the compound represented byFormula (E) in the coloring composition is preferably 0.1 to 10.0 mass%, more preferably 0.1 to 8.0 mass %, still more preferably 0.1 to 5.0mass %, and most preferably 0.1 to 3.0 mass % with respect to the totalmass of the coloring composition.

The total content (W₁+W_(D)+W_(E)) of the content (W₁) of the compoundrepresented by Formula (1), the content (W_(D)) of the compoundrepresented by Formula (D), and the content (W_(E)) of the compoundrepresented by Formula (E) in the coloring composition is preferably 1.0to 10.0 mass %, more preferably 1.0 to 8.0 mass %, still more preferably1.5 to 6.0 mass %, even still more preferably 1.0 to 5.0 mass %, andmost preferably 2.0 to 5.0 mass %.

By adjusting W₁+W_(D)+W_(E) to be 2.0 mass % or higher, the printingdensity of the ink on the recording medium during printing can beimproved. In addition, by adjusting W₁+W_(D)+W_(E) to be 5.0 mass % orlower, in a case where the coloring composition is used in an ink jetrecording method, the jettability is excellent, and an effect ofpreventing the clogging or the like of an ink jet nozzle can beobtained.

From the viewpoint of balance between color, saturation, adhesion(printing density), light fastness, ozone fastness, and moistureresistance, a mass ratio of the content of the compound represented byFormula (1) to the sum of the content of the compound representedFormula (D) and the content of the compound represented by Formula (E),that is, a mass ratio W₁/(W_(D)+W_(E)) is preferably 99/1 to 1/99, morepreferably 99/5 to 50/50, still more preferably 95/5 to 50/50, evenstill more preferably 90/10 to 50/50, and most preferably 90/10 to60/40.

The coloring composition according to the present invention optionallyincludes other additives within a range where the effects of the presentinvention are exhibited. The coloring composition according to thepresent invention can be preferably used as an ink jet recording ink.

[Ink Jet Recording Ink]

An ink jet recording ink can be prepared by dissolving and/or dispersingthe compound represented by Formula (1) and at least one compoundselected from the group consisting of the compound represented byFormula (D) and the compound represented by Formula (E) in a lipophilicmedium or an aqueous medium. In the ink jet recording ink, an aqueousmedium is preferably used.

In the ink jet recording ink, preferable ranges of the content of thecompound represented by Formula (1), the sum of the compound representedby Formula (D) and the compound represented by Formula (E), and the massratio of the content of the compound represented by Formula (1) to thesum of the compound represented by Formula (D) and the compoundrepresented by Formula (E) are the same as described above.

The ink jet recording ink according to the present invention optionallyincludes other additives within a range where the effects of the presentinvention are exhibited. Examples of the other additives includewell-known additives such as an anti-drying agent (wetting agent), anantifading agent, an emulsion stabilizer, a penetration enhancer, aultraviolet absorber, a preservative, a fungicide, a pH adjuster, asurface tension adjuster, an antifoaming agent, a viscosity adjuster, adispersant, a dispersion stabilizer, a rust inhibitor, a chelatingagent, or a betaine compound. In the case of a water-soluble ink, thesevarious additives can be directly added to the ink solution. In a casewhere an oil-soluble dye is used in the form of a dispersion, ingeneral, the additives are added to a dye dispersion after thepreparation of the dispersion. However, the additives may be added inthe form of an oil phase or a water phase during the preparation.

The anti-drying agent is preferably used to prevent clogging caused bythe ink jet recording ink being dried at an ink jetting port of a nozzleused in an ink jet recording method.

As the anti-drying agent, a water-soluble organic solvent having a lowervapor pressure than water is preferable. Specific examples of thewater-soluble organic solvent which is preferable to prevent dryinginclude: a polyhydric alcohol such as ethylene glycol, propylene glycol,diethylene glycol, polyethylene glycol, thiodiglycol, dithiodiglycol,2-methyl-1,3-propanediol, 1,2,6-hexanetriol, an acetylenic glycolderivative, glycerin, or trimethylolpropane; a polyhydric alcohol loweralkyl ether such as ethylene glycol monomethyl (or ethyl) ether,diethylene glycol monomethyl (or ethyl) ether, or triethylene glycolmonoethyl (or butyl) ether; a heterocycle such as 2-pyrrolidone,N-methyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone, orN-ethylmorpholine; a sulfur-containing compound such as sulfolane,dimethyl sulfoxide, or 3-sulfolane; a polyfunctional compound such asdiacetone alcohol or diethanolamine; and a urea derivative. Among these,a polyhydric alcohol such as glycerin or diethylene glycol is morepreferable. In addition, among the above-described anti-drying agents,one kind may be used alone, or a combination of two or more kinds may beused. The content of the anti-drying agent in the ink is preferably 10to 50 mass %.

The penetration enhancer is used in order to enhance the penetration ofthe ink jet recording ink into paper. As the penetration enhancer, forexample, an alcohol such as ethanol, isopropanol, butanol,di(tri)ethylene glycol monobutyl ether, or 1,2-hexanediol, sodium laurylsulfate, sodium oleate, or a nonionic surfactant can be used. Typically,the penetration enhancer sufficiently functions in a case where theaddition amount thereof is 5 to 30 mass %. It is preferable that thepenetration enhancer is used in an addition amount range where blurringof printed characters and images or page omission (print through) do notoccur.

The ultraviolet absorber can be used in order to improve storage ofimages. As the ultraviolet absorber, for example, a benzotriazolecompound described in JP1983-185677A (JP-S58-185677A), JP1986-190537A(JP-S61-190537A), JP1990-782A (JP-H2-782A), JP1993-197075A(JP-H5-197075A), and JP1997-34057A (JP-H9-34057A), a benzophenonecompound described in JP1971-2784A (JP-S46-2784A), JP1993-194483A(JP-H5-194483A), and U.S. Pat. No. 3,214,463A, a cinnamic acid compounddescribed in JP1973-30492B (JP-S48-30492B), JP1981-21141B(JP-S56-21141B), and JP1998-88106A (JP-H10-88106A), a triazine compounddescribed in JP1992-298503A (JP-H4-298503A), JP1996-53427A(JP-H8-53427A), JP1996-239368A (JP-H8-239368A). JP1999-182621A(JP-H10-182621A), and JP1996-501291A (JP-H8-501291A), a compounddescribed in Research Disclosure No. 24239, or a so-called fluorescencebrightening agent that is a compound that absorbs ultraviolet light toemit fluorescence such as a stilbene compound or a benzoxazol compoundcan also be used.

The antifading agent can be used in order to improve storage of images.As the antifading agent, various organic antifading agents or metalcomplexes can be used. Examples of the organic antifading agent includehydroquinones, alkoxyphenols, dialkoxyphenols, phenols, anilines,amines, indanes, chromans, alkoxyanilines, and heterocycles. Examples ofthe metal complex include a nickel complex and a zinc complex.Specifically, compounds described in the patents which are cited inSections I to J in No. VII in Research Disclosure No. 17643, ResearchDisclosure No. 15162, the left column in page 650 in Research DisclosureNo. 18716, page 527 in Research Disclosure No. 36544, page 872 inResearch Disclosure No. 307105, and Research Disclosure No. 15162, orcompounds which are included in formulae and compound examples ofrepresentative compounds described in page 127 to page 137 inJP1987-215272A (JP-S62-215272A) can be used.

Examples of the fungicide include sodium dehydroacetate, sodiumbenzoate, sodium pyridinethione-1-oxide, ethyl p-hydroxybenzoate ester,1,2-benzisothiazolin-3-one, and salts thereof. The amount of thefungicide used in the ink is preferably 0.02 to 1.00 mass %.

As the pH adjuster, a neutralizer (an organic base or an inorganicalkali) can be used. In order to improve storage stability of the inkjet recording ink, the pH adjuster is added such that the pH of the inkjet recording ink is preferably 6 to 10 and more preferably 7 to 10.

Examples of the surface tension adjuster include a nonionic surfactant,a cation surfactant, and an anionic surfactant. The surface tension ofthe ink jet recording ink according to the present invention ispreferably 25 to 70 mN/m and more preferably 25 to 60 mN/m. Theviscosity of the ink jet recording ink according to the presentinvention is preferably 30 mPa·s or lower and more preferably 20 mPa·sor lower. Preferable examples of the surfactant include: an anionicsurfactant such as an fatty acid salt, an alkylsulfonate, analkylbenzenesulfonate, an alkylnaphthalenesulfonate, adialkylsulfosuccinate, an alkylphosphate, a naphthalene sulfonic acidformalin condensate, or a polyoxyethylene alkylsulfonate; and a nonionicsurfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester,polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl amine,glycerin fatty acid ester, or an oxyethyleneoxypropylene blockcopolymer. In addition, SURFYNOLS (manufactured by AirProducts&Chemicals Inc.) that is an acetylene polyoxyethylene oxidesurfactant can also be preferably used. In addition, for example, anamine oxide amphoteric surfactant such as N,N-dimethyl-N-alkyl amineoxide is also preferable. Further, for example, surfactants which aredescribed in pp. 37 and 38 in JP1984-157636A (JP-S59-157636A) andResearch Disclosure No. 308119 (1989) can be used.

As the antifoaming agent, for example, a fluorine compound, a siliconecompound, or a chelating agent such as ethylenediaminetetraacetic acid(EDTA) can also be optionally used.

The betaine compound can be used in order to prevent image blurringunder a high-humidity condition. As the betaine compound, for example, acompound described in JP2004-285269A can be preferably used. Although apreferable range thereof varies depending on the kind thereof, theaddition amount of the betaine compound in the ink jet recording ink ispreferably 0.01 to 10.0 mass %, more preferably 0.01 to 5.0 mass %, andmost preferably 0.01 to 3.0 mass %.

As the aqueous medium, a mixture including water as a major componentand to which a water-miscible organic solvent is optionally added can beused. Examples of the water-miscible organic solvent include an alcohol(for example, methanol, ethanol, propanol, isopropanol, butanol,isobutanol, sec-butanol, t-butanol, pentanol, hexanol, cyclohexanol, orbenzyl alcohol), a polyhydric alcohol (for example, ethylene glycol,diethylene glycol, triethylene glycol, polyethylene glycol, propyleneglycol, dipropylene glycol, polypropylene glycol, butylene glycol,hexanediol, pentanediol, glycerin, hexanetriol, or thiodiglycol), aglycol derivative (for example, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, ethylene glycol monobutyl ether,diethylene glycol monomethyl ether, diethylene glycol monobutyl ether,propylene glycol monomethyl ether, propylene glycol monobutyl ether,dipropylene glycol monomethyl ether, triethylene glycol monomethylether, ethylene glycol diacetate, ethylene glycol monomethyl etheracetate, triethylene glycol monomethyl ether, triethylene glycolmonoethyl ether, or ethylene glycol monophenyl ether), an amine (forexample, ethanol amine, diethanol amine, triethanol amine, N-methyldiethanol amine, N-ethyl diethanol amine, morpholine, N-ethylmorpholine, ethylene diamine, diethylene triamine, triethylenetetramine, polyethyleneimine, or tetramethyl propylene diamine), andother polar solvents (for example, formamide, N,N-dimethyl formamide,N,N-dimethyl acetamide, dimethyl sulfoxide, sulfolane, 2-pyrrolidone,N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone, 2-oxazolidone,1,3-dimethyl-2-imidazolidinone, acetonitrile, or acetone). As thewater-miscible organic solvent, two or more kinds may be used incombination.

The viscosity of the ink jet recording ink according to the presentinvention is preferably 30 mPa·s or lower. In addition, the surfacetension of the ink for ink jet textile printing according to the presentinvention is preferably 25 mN/m to 70 mN/m. The viscosity and thesurface tension can be adjusted by adding various additives such as aviscosity adjuster, a surface tension adjuster, a specific resistanceadjuster, a film conditioner, an ultraviolet absorber, an antioxidant,an antifading agent, a fungicide, a rust inhibitor, a dispersant, and asurfactant.

The ink jet recording ink according to the present invention can be usedas any one of various color inks but is preferably used as a magentaink. In addition, the ink jet recording ink according to the presentinvention can be used not only for forming a monochromic image but alsofor forming a full-color image. In order to form a full-color image, amagenta ink, a cyan ink, and a yellow ink can be used. In addition, inorder to adjust the tone, a black ink may be further used.

The ink jet recording ink according to the present invention can be usedin a recording method such as printing, duplicating, marking, writing,drawing, or stamping and is particularly suitable in an ink jetrecording method.

[Ink Jet Recording Method]

In the ink jet recording method according to the present invention,energy is applied to the ink jet recording ink according to the presentinvention to form an image on a well-known image receiving material,that is, plain paper or resin coated paper, for example, ink jet paper,films, electrophotographic common paper, fabric, glass, metal, orceramic described in JP1996-169172A (JP-H8-169172A), JP1996-27693A(JP-H8-27693A), JP1990-276670A (JP-H2-276670A), JP1995-276789A(JP-H7-276789A), JP1997-323475A (JP-H9-323475A), JP1987-238783A(JP-S62-238783A), JP1998-153989A (JP-H10-153989A), JP1998-217473A(JP-H10-217473A), JP1998-235995A (JP-H10-235995A). JP1998-337947A(JP-H10-337947A), JP1998-217597A (JP-H10-217597A), and JP1998-337947A(JP-H10-337947A).

During the formation of an image, in order to impart glossiness andwater fastness or to improve weather fastness, a polymer particledispersion (also referred to as a polymer latex) may also be used.Regarding the timing when the polymer latex is added to the imagereceiving material, the addition may be performed before, during, orafter the addition of the colorants. Therefore, a position where theaddition is performed may be the image receiving paper or the ink.Alternatively, a liquid material consisting only of the polymer latexmay be used. Specifically, a method described in, for example,JP2000-363090. JP2000-315231, JP2000-354380. JP2000-343944,JP2000-268952, JP2000-299465, and JP2000-297365, can be preferably used.

[Ink Jet Printer Cartridge and Ink Jet Recorded Material]

An ink cartridge for ink jet recording according to the presentinvention is filled with the above-described ink jet recording inkaccording to the present invention. In addition, an ink jet recordedmaterial is obtained by forming a color image on a recording materialusing the ink jet recording ink according to the present invention.

The ink jet recording ink according to the present invention can be usedin well-known ink jet recording methods without any particularlimitation, for example, a charge control method of jetting ink using anelectrostatic attraction force, a drop-on-demand method (pressure pulsemethod) using a vibration pressure of a piezoelectric element, anacoustic ink jet method of jetting ink using a radiation pressure byconverting an electrical signal into an acoustic beam and irradiatingthe ink with the acoustic beam, or a thermal ink jet method of heatingink to form bubbles and using a pressure generated from the bubbles.Examples of the ink jet recording method include a method of jetting aplurality of droplets of a low-density ink called photo ink with a smallvolume, a method of improving image quality using a plurality of inkshaving substantially the same color and different densities, and amethod of using a colorless transparent ink.

EXAMPLES

Hereinafter, the present invention will be described using examples, butthe present invention is not limited to these examples. Unless specifiedotherwise, “%” and “part(s)” represent “mass %” and “part(s) by mass”.

SYNTHESIS EXAMPLES Synthesis of Exemplary Compound (1-11)

An exemplary compound (1-11) can be synthesized, for example, using thefollowing scheme.

Synthesis of Sulfofluorescein

76.4 g of saccharin and 100 g of concentrated sulfuric acid were addedto a 1 L three-neck flask at room temperature (20° C.), and the mixedsolution was heated to 120° C. 200 g of sulfolane and 103.3 g ofresorcin were added to the mixed solution. After the addition, the mixedsolution was heated to 140° C. and was stirred at 140° C. for 20 hours.Next, the obtained reaction solution was cooled to 20° C. for 1 hour.After cooling, 500 g of water was added to the reaction solution for 30minutes. After the addition, the reaction solution was stirred for 30minutes. The obtained suspension was filtered, and the obtained crystalswere washed with 130 mL of water four times. After washing, the crystalswere dried by blowing air at 50° C. for 20 hours. As a result, 68.5 g ofsulfofluorescein was obtained as yellow crystals (yield: 45%).

Synthesis of DCSF

36.8 g of sulfofluorescein and 150 g of phosphorus oxychloride wereadded to a 200 mL three-neck flask. The mixture was heated to 105° C.and was stirred at 105° C. for 18 hours. Next, the obtained reactionsolution was cooled to 20° C. for 1 hour. The obtained reaction solutionwas added to a 2 L three-neck flask to which 1 L of water was added for20 minutes while cooling the flask in a water bath at 20° C. such thatthe water temperature did not exceed 35° C. After the addition, thereaction solution was stirred at 20° C. for 1 hour. The obtainedsuspension was filtered, and the obtained crystals were washed with 200mL of water once and then was washed with 200 mL of acetonitrile twice.After washing, the crystals were dried by blowing air at 50° C. for 18hours. As a result, 22.7 g of dichloro sulfonphthalein (DCSF) wasobtained (yield: 56%).

Synthesis of Intermediate Product (A)

30 g of dichloro sulfonphthalein (DCSF), 63 g of2,4,6-trimethyl-1,3-phenylenediamine (manufactured by Tokyo ChemicalIndustry Co., Ltd.), and 11 g of zinc chloride were added to 265 g ofethylene glycol, and the components were caused to react with each otherat 150° C. for 6 hours. The reaction solution was cooled to roomtemperature, and 300 mL of 0.6 mol/L hydrochloric acid was addeddropwise to precipitate crystals. The precipitated crystals wereseparated by filtration and were washed with 300 mL of water. Theobtained crystals were dried at 60° C. for 12 hours to obtain crystalsof an intermediate (A).

Yield amount: 23 g

Yield: 50%

Mass spectrum (MS) (m/z)=633 ([M+1]+, 100%)

Synthesis of Intermediate (B)

23.0 g of the intermediate (A) was added to 420 g of 10% fuming sulfuricacid, and the components were caused to react with each other at roomtemperature for 48 hours. The reaction solution was poured into a largeexcess of ethyl acetate, and precipitated crystals was separated byfiltration. The separated crystals were dissolved in 500 mL of methanol,the solution was adjusted to pH 7 using a 28% sodium methoxide methanolsolution, and precipitated sodium sulfate was removed by filtration.Next, the filtrate was condensed and dried using a rotary evaporator.The obtained residue was purified by column chromatography (filler:SEPHADEX LH-20 (manufactured by Pharmacia)), developing solvent:methanol) to obtain crystals of an intermediate (B).

Yield amount: 21.0 g

Yield: 68%

Mass spectrum (MS) (m/z)=793 ([M−2Na+H]⁻, 100%)

Synthesis of Exemplary Compound (1-11)

3.0 g of the intermediate (B) was dissolved in 15 mL of ultrapure water,and the reaction solution was cooled to an internal temperature of 10°C. or lower. 2.55 g of powder of 5-(chlorosulfonyl)salicylic acid(synthesized using a method described in German Patent No. DE264786) wasadded, 10% NaOH aqueous solution was added dropwise at an internaltemperature of 10° C. or lower such that the pH of the reaction solutionwas maintained at 8.0, and the dropwise addition was continued until thepH did not change. The obtained reaction solution was poured into alarge excess of isopropyl alcohol, and precipitated solid was separatedby filtration. The obtained solid was dissolved in 20 mL of a mixedsolvent (water/methanol=1/1). Next, the obtained solution was purifiedby column chromatography (filler: SEPHADEX LH-20 (manufactured byPharmacia), developing solvent: water/methanol). Next, an inorganic saltand a residual organic solvent were removed using a dialysis membrane(molecular weight cutoff: 3500, Spectra/Por 3 Dialysis Membrane (tradename, manufactured by Spectrum, Inc.)). The pH of the obtained aqueoussolution was adjusted to 7 using a diluted sodium hydroxide aqueoussolution, and dust was removed by filtration using a membrane filter.The obtained aqueous solution was condensed and dried using a rotaryevaporator. As a result, green glossy crystals of the exemplary compound(1-11) were obtained.

Yield amount: 1.5 g

Yield: 33%

MS (m/z)=1191 ([M−1]⁻, 100%)

In an absorption spectrum of the exemplary compound (1-11) in the diluteaqueous solution, the absorption maximum was 532 nm, and the molarabsorption coefficient was 87000. FIG. 1 is a diagram showing a ¹H-NMRspectrum of the exemplary compound (1-11) in dimethyl sulfoxide-d6.

(Synthesis of Exemplary Compound (1-18))

An exemplary compound (1-18) can be synthesized, for example, using thefollowing scheme.

3.0 g of the intermediate (B) obtained as the synthetic intermediate ofthe exemplary compound (1-11) described above was dissolved in 15 mL ofultrapure water, and the obtained solution was cooled to an internaltemperature of 10° C. or lower. 2.2 g of powder of5-chlorosulfonyl-3-hydroxy-2-naphthoic acid (synthesized using a methoddescribed in German Patent No. DE264786) was added, 10% NaOH aqueoussolution was added dropwise at an internal temperature of 10° C. orlower such that the pH of the reaction solution was maintained at 7.5,and the dropwise addition was continued until the pH did not change. Theobtained reaction solution was poured into a large excess of isopropylalcohol, and precipitated solid was separated by filtration. Theobtained solid was dissolved in 20 mL of a mixed solvent(water/methanol=1/1). Next, the obtained solution was purified by columnchromatography (filler: SEPHADEX LH-20 (manufactured by Pharmacia),developing solvent: water/methanol). Next, an inorganic salt and aresidual organic solvent were removed using a dialysis membrane(molecular weight cutoff: 3500, Spectra/Por 3 Dialysis Membrane (tradename, manufactured by Spectrum, Inc.)). The pH of the obtained aqueoussolution was adjusted to 7 using a diluted sodium hydroxide aqueoussolution, and dust was removed by filtration using a membrane filter.The obtained aqueous solution was condensed and dried using a rotaryevaporator. As a result, green glossy crystals of the exemplary compound(1-18) were obtained.

Yield amount: 1.2 g

Yield: 24%

MS (m/z)=1291 ([M−1]⁻, 100%)

In an absorption spectrum of the exemplary compound (1-18) in the diluteaqueous solution, the absorption maximum was 532 nm, and the molarabsorption coefficient was 85000. FIG. 2 is a diagram showing a ¹H-NMRspectrum of the exemplary compound (1-18) in dimethyl sulfoxide-d6.

(Synthesis of Exemplary Compound (1-25))

An exemplary compound (1-25) can be synthesized, for example, using thefollowing scheme.

3.0 g of the intermediate (B) obtained as the synthetic intermediate ofthe exemplary compound (1-11) described above was dissolved in 15 mL ofultrapure water, and the obtained solution was cooled to an internaltemperature of 10° C. or lower. 2.2 g of powder of6-chlorosulfonyl-2-hydroxy-1-naphthoic acid (synthesized using a methoddescribed in German Patent No. DE278091) was added, 10% NaOH aqueoussolution was added dropwise at an internal temperature of 10° C. orlower such that the pH of the reaction solution was maintained at 7.5,and the dropwise addition was continued until the pH did not change. Theobtained reaction solution was poured into a large excess of isopropylalcohol, and precipitated solid was separated by filtration. Theobtained solid was dissolved in 20 mL of a mixed solvent(water/methanol=1/1). Next, the obtained solution was purified by columnchromatography (filler: SEPHADEX LH-20 (manufactured by Pharmacia),developing solvent: water/methanol). Next, an inorganic salt and aresidual organic solvent were removed using a dialysis membrane(molecular weight cutoff: 3500, Spectra/Por 3 Dialysis Membrane (tradename, manufactured by Spectrum. Inc.)). The pH of the obtained aqueoussolution was adjusted to 7 using a diluted sodium hydroxide aqueoussolution, and dust was removed by filtration using a membrane filter.The obtained aqueous solution was condensed and dried using a rotaryevaporator. As a result, green glossy crystals of the exemplary compound(1-25) were obtained.

Yield amount: 1.3 g

Yield: 26%

MS (m/z)=1291 ([M−1]⁻, 100%)

In an absorption spectrum of Exemplary Compound (1-25) in the diluteaqueous solution, the absorption maximum was 532 nm, and the molarabsorption coefficient was 83000.

(Synthesis of Exemplary Compound (1-26))

An exemplary compound (1-26) can be synthesized, for example, using thefollowing scheme.

3.0 g of the intermediate (B) obtained as the synthetic intermediate ofthe exemplary compound (1-11) described above was dissolved in 15 mL ofultrapure water, and the obtained solution was cooled to an internaltemperature of 10° C. or lower. 2.7 g of powder of5-chlorosulfonyl-4-hydroxyisophthalic acid (synthesized using a methoddescribed in German Patent No. DE264786) was added, 10% NaOH aqueoussolution was added dropwise at an internal temperature of 10° C. orlower such that the pH of the reaction solution was maintained at 7.5,and the dropwise addition was continued until the pH did not change. Theobtained reaction solution was poured into a large excess of isopropylalcohol, and precipitated solid was separated by filtration. Theobtained solid was dissolved in 20 mL of a mixed solvent(water/methanol=1/1). Next, the obtained solution was purified by columnchromatography (filler: SEPHADEX LH-20 (manufactured by Pharmacia),developing solvent: water/methanol). Next, an inorganic salt and aresidual organic solvent were removed using a dialysis membrane(molecular weight cutoff: 3500, Spectra/Por 3 Dialysis Membrane (tradename, manufactured by Spectrum, Inc.)). The pH of the obtained aqueoussolution was adjusted to 7 using a diluted sodium hydroxide aqueoussolution, and dust was removed by filtration using a membrane filter.The obtained aqueous solution was condensed and dried using a rotaryevaporator. As a result, green glossy crystals of the exemplary compound(1-26) were obtained.

Yield amount: 1.8 g

Yield: 36%

MS (m/z)=1279 ([M−1]⁻; 100%)

In an absorption spectrum of Exemplary Compound (1-26) in the diluteaqueous solution, the absorption maximum was 534 nm, and the molarabsorption coefficient was 95000. FIG. 3 is a diagram showing a ¹H-NMRspectrum of the exemplary compound (1-26) in dimethyl sulfoxide-d6.

(Synthesis of Exemplar) Compound (1-30))

An exemplary compound (1-30) can be synthesized, for example, using thefollowing scheme.

3.0 g of the intermediate (B) obtained as the synthetic intermediate ofthe exemplary compound (1-11) described above was dissolved in 15 mL ofultrapure water. 2.2 g of powder of dimethyl5-(chlorosulfonyl)isophthalate (synthesized using a method described inGerman Patent No. DE278091) was added, 10% NaOH aqueous solution wasadded dropwise such that the pH of the reaction solution was maintainedat 5 to 7, and the dropwise addition was continued until the pH did notchange. After completion of the reaction, 3 mL of 50% NaOH aqueoussolution was added and stirred for 1 hour. The obtained reactionsolution was poured into a large excess of ethanol, and precipitatedsolid was separated by filtering. The obtained solid was dissolved in 20mL of a mixed solvent (water/methanol=1/1). Next, the obtained solutionwas purified by column chromatography (filler: SEPHADEX LH-20(manufactured by Pharmacia), developing solvent: water/methanol). Next,an inorganic salt and a residual organic solvent were removed using adialysis membrane (molecular weight cutoff: 3500, Spectra/Por 3 DialysisMembrane (trade name, manufactured by Spectrum, Inc.)). The pH of theobtained aqueous solution was adjusted to 7 using a diluted sodiumhydroxide aqueous solution, and dust was removed by filtration using amembrane filter. The obtained aqueous solution was condensed and driedusing a rotary evaporator. As a result, green glossy crystals of theexemplary compound (1-30) were obtained.

Yield amount: 3.7 g

Yield: 70%

MS (m/z)=1247 ([M−1]⁻, 100%)

In an absorption spectrum of Exemplary Compound (1-30) in the diluteaqueous solution, the absorption maximum was 532 nm, and the molarabsorption coefficient was 82000. FIG. 4 is a diagram showing a ¹H-NMRspectrum of the exemplary compound (1-30) in dimethyl sulfoxide-d6.

Other Exemplary Compounds can be synthesized using the above-describedmethod.

The following compound (d-1) was synthesized with reference toJP2003-192930A, and the following compound (e-1) was synthesized withreference to WO2004/104108A. Other exemplary compounds (d-2) and (d-3)can be synthesized using the above-described method.

Example 1

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 1 for magenta was prepared. “Compound of Formula (1)”refers to a compound represented by Formula (1), “Compound of Formula(D)” refers to a compound represented by Formula (D), and “Compound ofFormula (E)” refers to a compound represented by Formula (E).

Compound of Formula (1) (exemplary compound (1-11)) 2.25 g Compound ofFormula (D) (exemplary compound (d-1)) 0.75 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 10.00 g  Triethylene glycol 2.00g Triethylene glycol monobutyl ether 10.00 g  2-pyrrolidone 2.00 gSURFYNOL (manufactured by Air Products&Chemicals Inc.) 1.00 g

Example 2

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 2 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 2.25 g Compound ofFormula (D) (exemplary compound (d-1)) 0.75 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 (betaine compound having thefollowing structure) 1.28 g Glycerin 10.00 g  Triethylene glycol 2.00 gTriethylene glycol monobutyl ether 10.00 g  2-pyrrolidone 2.00 gSURFYNOL (manufactured by Air Products&Chemicals Inc.) 1.00 g

Example 3

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 3 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 2.25 g Compound ofFormula (D) (exemplary compound (d-1)) 0.75 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-2 (betaine compound having thefollowing structure) 1.28 g Glycerin 10.00 g  Triethylene glycol 2.00 gTriethylene glycol monobutyl ether 10.00 g  2-pyrrolidone 2.00 gSURFYNOL (manufactured by Air Products&Chemicals Inc.) 1.00 g

Example 4

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 4 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 2.00 g Compound ofFormula (D) (exemplary compound (d-1)) 1.00 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.14 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 5

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 5 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 1.75 g Compound ofFormula (D) (exemplary compound (d-1)) 1.25 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 6

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 6 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 1.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 7

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 7 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 3.00 g Compound ofFormula (D) (exemplary compound (d-1)) 1.00 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 8

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 8 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 2.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 9

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 9 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 3.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 10

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 pun. As a result, an inkjet recording ink 10 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 2.50 g Compound ofFormula (D) (exemplary compound (d-1)) 2.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Betaine-1 1.00 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Example 11

An ink jet recording ink 11 was prepared through the same operation asin Example 2, except that the exemplary compound (1-18) was used insteadof the exemplary compound (1-11).

Example 12

An ink jet recording ink 12 was prepared through the same operation asin Example 2, except that the exemplary compound (1-19) was used insteadof the exemplary compound (1-11).

Example 13

An ink jet recording ink 13 was prepared through the same operation asin Example 2, except that the exemplary compound (1-20) was used insteadof the exemplary compound (1-11).

Example 14

An ink jet recording ink 14 was prepared through the same operation asin Example 2, except that the exemplary compound (1-25) was used insteadof the exemplary compound (1-11).

Example 15

An ink jet recording ink 15 was prepared through the same operation asin Example 1, except that the exemplary compound (1-26) was used insteadof the exemplary compound (1-11).

Example 16

An ink jet recording ink 16 was prepared through the same operation asin Example 2, except that the exemplary compound (1-26) was used insteadof the exemplary compound (1-11).

Example 17

An ink jet recording ink 17 was prepared through the same operation asin Example 2, except that the exemplary compound (1-29) was used insteadof the exemplary compound (1-11).

Example 18

An ink jet recording ink 18 was prepared through the same operation asin Example 1, except that the exemplary compound (1-30) was used insteadof the exemplary compound (1-11).

Example 19

An ink jet recording ink 19 was prepared through the same operation asin Example 2, except that the exemplary compound (1-30) was used insteadof the exemplary compound (1-11).

Example 20

An ink jet recording ink 20 was prepared through the same operation asin Example 2, except that the exemplary compound (1-34) was used insteadof the exemplary compound (1-11).

Example 21

An ink jet recording ink 21 was prepared through the same operation asin Example 1, except that the exemplary compound (1-35) was used insteadof the exemplary compound (1-11).

Example 22

An ink jet recording ink 22 was prepared through the same operation asin Example 2, except that the exemplary compound (1-35) was used insteadof the exemplary compound (1-11).

Example 23

An ink jet recording ink 23 was prepared through the same operation asin Example 1, except that the exemplary compound (d-2) was used insteadof the exemplary compound (d-1).

Example 24

An ink jet recording ink 24 was prepared through the same operation asin Example 2, except that the exemplary compound (d-3) was used insteadof the exemplary compound (d-1).

Example 25

An ink jet recording ink 25 was prepared through the same operation asin Example 2, except that the exemplary compound (e-1) was used insteadof the exemplary compound (d-1).

Example 26

An ink jet recording ink 26 was prepared through the same operation asin Example 16, except that the exemplary compound (d-2) was used insteadof the exemplary compound (d-1).

Example 27

An ink jet recording ink 27 was prepared through the same operation asin Example 19, except that the exemplary compound (d-3) was used insteadof the exemplary compound (d-1).

Example 28

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 28 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 2.25 g Compound ofFormula (D) (exemplary compound (d-1)) 0.75 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 29

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 29 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 2.25 g Compound ofFormula (D) (exemplary compound (d-1)) 0.75 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 30

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 30 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 2.00 g Compound ofFormula (D) (exemplary compound (d-1)) 1.00 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 31

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 31 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 2.00 g Compound ofFormula (D) (exemplary compound (d-1)) 1.00 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 32

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 32 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 1.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 33

Deionized water was added to the following components such that thebalance was 100) g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 33 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 2.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Example 34

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 34 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 3.00 g Compound ofFormula (D) (exemplary compound (d-1)) 2.00 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products Chemicals Inc.) 0.50 g

Example 35

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, an inkjet recording ink 35 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 3.50 g Compound ofFormula (D) (exemplary compound (d-1)) 1.50 g PROXEL XLII (preservative,manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethylene urea 7.00 g1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 0.50 g

Comparative Example 1

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 1 for magenta was prepared.

Compound of Formula (D) (exemplary compound (d-1)) 3.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Comparative Example 2

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 2 for magenta was prepared.

Compound of Formula (D) (exemplary compound (d-1)) 3.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Betaine-1 1.43 g Glycerin10.00 g  Triethylene glycol 2.00 g Triethylene glycol monobutyl ether10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured by AirProducts&Chemicals Inc.) 1.00 g

Comparative Example 3

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 3 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-11)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Comparative Example 4

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 4 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Comparative Example 5

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 5 for magenta was prepared.

Compound of Formula (a) (exemplary compound (d-1)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Comparative Example 6

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 6 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 0.50 g Compound ofFormula (1) (exemplary compound (1-30)) 0.50 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 10.00 g Triethylene glycol 2.00 g Triethylene glycol monobutyl ether 10.00 g 2-pyrrolidone 2.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 1.00 g

Comparative Example 7

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 7 for magenta was prepared.

Comparative compound 1 2.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 10.00 g  Triethylene glycol 2.00 g Triethylene glycolmonobutyl ether 10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 1.00 g

Comparative Example 8

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 8 for magenta was prepared.

Comparative compound 2 2.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 10.00 g  Triethylene glycol 2.00 g Triethylene glycolmonobutyl ether 10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 1.00 g

Comparative Example 9

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 9 for magenta was prepared.

Comparative compound 3 2.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 10.00 g  Triethylene glycol 2.00 g Triethylene glycolmonobutyl ether 10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 1.00 g

Comparative Example 10

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 10 for magenta was prepared.

Comparative compound 4 3.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 10.00 g  Triethylene glycol 2.00 g Triethylene glycolmonobutyl ether 10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 1.00 g

Comparative Example 11

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 11 for magenta was prepared.

Comparative compound 5 3.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 10.00 g  Triethylene glycol 2.00 g Triethylene glycolmonobutyl ether 10.00 g  2-pyrrolidone 2.00 g SURFYNOL (manufactured byAir Products&Chemicals Inc.) 1.00 g

Comparative Example 12

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 12 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-26)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethyleneurea 7.00 g 1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL(manufactured by Air Products&Chemicals Inc.) 0.50 g

Comparative Example 13

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 13 for magenta was prepared.

Compound of Formula (1) (exemplary compound (1-30)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethyleneurea 7.00 g 1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL(manufactured by Air Products&Chemicals Inc.) 0.50 g

Comparative Example 14

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 14 for magenta was prepared.

Compound of Formula (D) (exemplary compound (d-1)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethyleneurea 7.00 g 1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL(manufactured by Air Products&Chemicals Inc.) 0.50 g

Comparative Example 15

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 15 for magenta was prepared.

Compound of Formula (D) (exemplary compound (d-2)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethyleneurea 7.00 g 1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL(manufactured by Air Products&Chemicals Inc.) 0.50 g

Comparative Example 16

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 16 for magenta was prepared.

Compound of Formula (E) (exemplary compound (e-1)) 1.00 g PROXEL XLII(preservative, manufactured by Lonza) 0.11 g Glycerin 7.00 g Ethyleneurea 7.00 g 1,5-pentanediol 7.00 g 2-pyrrolidone 5.00 g SURFYNOL(manufactured by Air Products&Chemicals Inc.) 0.50 g

Comparative Example 17

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 17 for magenta was prepared.

Comparative compound 1 2.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 7.00 g Ethylene urea 7.00 g 1,5-pentanediol 7.00 g2-pyrrolidone 5.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 0.50 g

Comparative Example 18

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 18 for magenta was prepared.

Comparative compound 1 2.25 g Compound of Formula (E) (exemplarycompound (e-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 7.00 g Ethylene urea 7.00 g 1,5-pentanediol 7.00 g2-pyrrolidone 5.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 0.50 g

Comparative Example 19

Deionized water was added to the following components such that thebalance was 100 g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 19 for magenta was prepared.

Comparative compound 3 2.25 g Compound of Formula (D) (exemplarycompound (d-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 7.00 g Ethylene urea 7.00 g 1,5-pentanediol 7.00 g2-pyrrolidone 5.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 0.50 g

Comparative Example 20

Deionized water was added to the following components such that thebalance was 10) g, and the components were stirred for 1 hour whileheating them at 30° C. to 40° C. Next, the pH of the solution wasadjusted to 8.5 using 10 mol/L of sodium hydroxide aqueous solution, andthe obtained solution was filtered under reduced pressure through amicrofilter having an average pore size of 0.20 μm. As a result, acomparative ink jet recording ink 20 for magenta was prepared.

Comparative compound 3 2.25 g Compound of Formula (E) (exemplarycompound (e-1)) 0.75 g PROXEL XLII (preservative, manufactured by Lonza)0.11 g Glycerin 7.00 g Ethylene urea 7.00 g 1,5-pentanediol 7.00 g2-pyrrolidone 5.00 g SURFYNOL (manufactured by Air Products&ChemicalsInc.) 0.50 g

(Image Formation and Evaluation)

Using each of the ink jet recording inks prepared as described above, animage was formed and was evaluated as described below. In each ofExamples and Comparative Examples, an image was formed and evaluatedusing a combination of an ink jet printer and a recording paper shownbelow.

The ink jet recording inks 1 to 27 according to Examples and thecomparative ink jet recording inks 1 to 11 according to ComparativeExamples were evaluated as follows. The results are shown in Tables 5and 6 below.

Tables 5 and 6 show the results of the respective evaluations performedafter filling an ink cartridge with each of the ink jet recording inksand recording an image on photographic paper (“KOUTAKU”, manufactured bySeiko Epson Corporation) using an ink jet printer (PM-700C, manufacturedby Seiko Epson Corporation)

The ink jet recording inks 28 to 35 according to Examples and thecomparative ink jet recording inks 12 to 20 according to ComparativeExamples were evaluated as follows. The results are shown in Table 6below. Table 6 shows the results of the respective evaluations performedafter filling an ink cartridge with each of the ink jet recording inksand recording an image on photographic paper (photo glossy paper PT-201,manufactured by Canon Corporation) using an ink jet printer (PIXUS Pro9000 Mk II, manufactured by Canon Corporation).

<Color>

In a case where the color of a printed sample was determined by visualinspection, a sample having a color of pure magenta was evaluated as“A”, a sample having a color of reddish magenta was evaluated as “B”,and a sample having a color of reddish violet was evaluated as “C”.

<Saturation>

The saturation (C*) of a printed material was calculated according tothe following expression based on measurement of color characteristics.Using a reflection densitometer (trade name: X-Rite 310TR, manufacturedby X-Rite Inc.), the lightness L* and the chromaticity a* and b* of aprinted image portion at an applied voltage of 50% were measuredaccording to the CIE L*a*b* color system (International Commission onIllumination (1976) or JIS (Japanese Industrial Standards)Z8781-4:2013)). The saturation (C*) was obtained from the obtainedvalues according to the following calculation expression and wasevaluated based on the following evaluation criteria.Saturation (C*)=(a* ² +b* ²)^(1/2)

A: C* was 90 or higher

B: C* was 80 or higher and lower than 90

C: C* was lower than 80

<Printing Density>

Using the above-described combination of the ink jet printer and therecording paper and each of the ink jet recording inks, a solid image(printed image at an applied voltage of 100%) was formed.

The printing density of the formed solid image was measured using areflection densitometer (trade name: X-Rite 310 TR, manufactured byX-Rite Inc.). A solid image having a printing density of 2.0 or higherwas evaluated as “A”, a solid image having a printing density of 1.8 orhigher and lower than 2.0 was evaluated as “B”, a solid image having aprinting density of 1.7 or higher and lower than 1.8 was evaluated as“C”, and a solid image having a printing density of lower than 1.7 wasevaluated as “D”.

<Light Fastness>

Immediately after the formation of the solid image, an image density Ciwas measured. Next, the image was irradiated with xenon light (100000lux) for 28 hours using a weather meter (ATLAS C.165), and then an imagedensity Cf1 was measured again. Based on the image density values beforeand after the irradiation of the xenon light, a coloring agent residuerate was calculated and evaluated. The image density was measured usinga reflection densitometer (trade name: X-Rite 310TR, manufactured byX-rite). The coloring agent residue rate was measured in an imageportion where the initial image density was 1.0±0.2.

The coloring agent residue rate was obtained according to the followingexpression, and light fastness was evaluated based on the followingevaluation criteria.Coloring Agent Residue Rate (%)=(Cf1/Ci)×100

A: the coloring agent residue rate was 90% or higher and lower than 95%

B: the coloring agent residue rate was 80% or higher and lower than 90%

C: the coloring agent residue rate was lower than 80%

<Ozone Fastness>

A 5 kV alternating current voltage was applied while causing dry air toflow through the inside of a double glass tube of an ozonizer(manufactured by Siemens AG). The recording paper on which the image wasformed was left to stand for 3 days in a box having an ozone gasconcentration of 5±0.1 ppm that was set in a dark place at roomtemperature using the ozonizer. Next, the image density was measuredusing a reflection densitometer (trade name: X-Rite 310TR, manufacturedby X-rite) before and after leaving the recording paper to stand inozone gas. Based on an initial image density Ci and an image density Cf2measured after leaving the recording paper to stand in ozone gas, acoloring agent residue rate was calculated and evaluated.

The coloring agent residue rate was measured in an image portion wherethe initial image density was 1.0±0.2. The ozone gas concentration inthe box was set using an ozone gas monitor (Mode: OZG-EM-01,manufactured by Applics Corporation).

The coloring agent residue rate was obtained according to the followingexpression, and ozone fastness was evaluated based on the followingevaluation criteria.Coloring Agent Residue Rate (%)=(Cf2/Ci)×100

A: the coloring agent residue rate was 85% or higher and lower than 90%

B: the coloring agent residue rate was 80% or higher and lower than 85%

C: the coloring agent residue rate was lower than 80%

<Moisture Resistance>

Regarding image blurring under high-humidity conditions, a 3 cm×3 cmprinting pattern was prepared by disposing 1 mm×1 mm magenta squaressuch that 0.5 mm white spaces were formed between the squares. Afterstoring this image sample under conditions of 45° C. and a relativehumidity of 80% for 7 days, the blurring of the magenta dye was observedin the white spaces.

Specifically, the OD value of the printed material before (immediatelybefore printing) the exposure to the conditions (conditions of 45° C.and a relative humidity of 80%) and the OD value of the printed materialafter the storage under the conditions for 7 days were measured using areflection densitometer “Spectrilino” (trade name, manufactured byGretag Macbeth GmbH), and an increase in the magenta density of thewhite space after the storage under the conditions for 7 days from themagenta density immediately after the printing was measured in a greenfilter of Status A. A case where the measured value was lower than 0.02was evaluated as “A”, a case where the measured value was 0.02 or higherand lower than 0.05 was evaluated as “B”, a case where the measuredvalue was 0.05 or higher and lower than 0.10 was evaluated as “C”, and acase where the measured value was 0.10 or higher was evaluated as “D”.

<Jetting Stability>

First, immediately after the preparation of each of the ink jetrecording inks, the ink jetted from all the nozzles of the ink jetprinter was observed using the combination of the ink jet printer andthe recording paper. Next, printing was performed on 100 pieces for eachof the recording papers, and the following evaluation was performedbased on the following criteria. In all the Examples and ComparativeExamples, the evaluation results were “A”. The size of the recordingpaper used was A4.

Next, each of the ink jet recording inks was stored under conditions of40° C. and a relative humidity of 80% for 2 weeks, and then each of theink jet recording inks jetted from all the nozzles of the ink jetprinter was observed using the combination of the ink jet printer andthe recording paper (the size of the recording paper was A4). Next,printing was performed on 100 pieces for each of the recording papers,and jetting stability was evaluated based on the following criteria.

The results are shown in Tables 5 and 6 below.

A: Substantially no irregularities of characters was found from thestart to the end of printing

B: irregularities of characters were found on some pieces of therecording paper

C: irregularities of characters were found was found from the start tothe end of printing

TABLE 5 Print- ing Light Ozone Moisture Jetting Satu- Den- Fast- Fast-Resis- Stabil- Color ration sity ness ness tance ity Example 1 A A A A AB A Example 2 A A A A A A A Example 3 A A A A A A A Example 4 C B A A AA A Example 5 C B A A A A A Example 6 C B A B B A A Example 7 A A A A AA A Example 8 C B A A A A A Example 9 A A A A A A A Example 10 C B A B BA A Example 11 A A A A A A A Example 12 A A A A A A A Example 13 A A A AA A A Example 14 A A A A A A A Example 15 A A A A A A A Example 16 A A AA A A A Example 17 A A A A A A A Example 18 A A A A A B A Example 19 A AA A A A A Example 20 A A A A A A A Example 21 A A A A A B A Example 22 AA A A A A A Example 23 A A A A A B A Example 24 A A A A A A A Example 25A A A A A A A Example 26 A A A A A A A Example 27 A A A A A A A

TABLE 6 Print- ing Light Ozone Moisture Jetting Satu- Den- Fast- Fast-Resis- Stabil- Color ration sity ness ness tance ity Example 28 A A A AA A A Example 29 A A A A A A A Example 30 C B A A A A A Example 31 C B AA A A A Example 32 C B A B B A A Example 33 C B A A A A A Example 34 C BA A A A A Example 35 A A A A A A A Comparative C C C B C A A Example 1Comparative C C C B C A A Example 2 Comparative A A C B B B A Example 3Comparative A A C B B B A Example 4 Comparative C C C B B A A Example 5Comparative A A C B B A A Example 6 Comparative A A A C C C A Example 7Comparative A A A C B C A Example 8 Comparative C C D C C B B Example 9Comparative A A A B B C A Example 10 Comparative A A A B B C A Example11 Comparative A A C B B A A Example 12 Comparative A A C B B A AExample 13 Comparative C C C B B A A Example 14 Comparative C C C B B AA Example 15 Comparative C C C B B A A Example 16 Comparative A A A C CC A Example 17 Comparative A A A C C C A Example 18 Comparative C C C BB B B Example 19 Comparative C C C B B C B Example 20

As can be seen from the results of Tables 5 and 6, each of the inksaccording to Examples in which the compound according to the presentinvention was used were excellent in all the evaluations of color,saturation, adhesion (printing density), light fastness, ozone fastness,moisture resistance, and jetting stability.

INDUSTRIAL APPLICABILITY

According to the present invention, it is possible to provide: acoloring composition with which an image having excellent color,saturation, and adhesion (printing density) and having excellent lightfastness, ozone fastness, and moisture resistance can be formed and thathas excellent jetting stability in an ink jet printer; an ink jetrecording ink including the coloring composition; an ink jet recordingmethod using the ink jet recording ink; and an ink jet printer cartridgethat is filled with the ink jet recording ink.

The present invention has been described in detail with reference to thespecific embodiment. However, it is obvious to those skilled in the artthat various modifications and changes can be made within a range notdeparting from the scope of the present invention.

What is claimed is:
 1. A coloring composition comprising: a compoundrepresented by the following Formula (1); and at least one compoundselected from the group consisting of a compound represented by thefollowing Formula (D) and a compound represented by the followingFormula (E),

in Formula (1), R¹, R⁵, R⁶, and R¹⁰ each independently represent analkyl group, R⁴, R⁹, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, R¹⁹, andR²⁰ each independently represent a hydrogen atom or a substituent, R²,R³, R⁷, and R⁸ each independently represent a hydrogen atom, an alkylgroup, or a substituent represented by the following Formula (A), and atleast one of R², R³, R⁷, or R⁸ represents a substituent represented bythe following Formula (A),

in Formula (A), X represents a substituent represented by the followingFormula (X1), (X2), or (X3), and * represents a direct bond to a benzenering,

in Formula (X1), R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ each independentlyrepresent a hydrogen atom or a substituent, R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, andR⁴⁰⁵ satisfy the following condition (i) or (ii), * represents a directbond to a sulfur atom, the condition (i): at least one of R⁴⁰¹, R⁴⁰²,R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a hydroxyl group and at least one ofR⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵ represents a carboxyl group, and thecondition (ii): at least two of R⁴⁰¹, R⁴⁰², R⁴⁰³, R⁴⁰⁴, or R⁴⁰⁵represent a carboxyl group,

in Formula (X2), R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ eachindependently represent a hydrogen atom or a substituent, R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ satisfy the following condition (iii)or (iv), * represents a direct bond to a sulfur atom, the condition(iii): at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷represents a hydroxyl group and at least one of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴,R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷ represents a carboxyl group, and the condition (iv):at least two of R⁵⁰¹, R⁵⁰², R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, or R⁵⁰⁷ represent acarboxyl group,

in Formula (X3), R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ eachindependently represent a hydrogen atom or a substituent, R⁶⁰¹, R⁶⁰²,R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ satisfy the following condition (v) or(vi), * represents a direct bond to a sulfur atom, the condition (v): atleast one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represents ahydroxyl group and at least one of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶,or R⁶⁰⁷ represents a carboxyl group, and the condition (vi): at leasttwo of R⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, or R⁶⁰⁷ represent a carboxylgroup,

in Formula (D), R₂₁ and R₂₂ each independently represent a hydrogen atomor a substituted or unsubstituted alkyl group, Y₂₁ and Y₂₂ eachindependently represent a chlorine atom, a hydroxyl group, a substitutedor unsubstituted amino group, an alkoxy group, a substituted orunsubstituted phenoxy group, or a substituted or unsubstitutednaphthyloxy group, Xd represents a divalent linking group, M⁴ representsa hydrogen atom or a counter cation, and M⁴′s may be the same as ordifferent from each other,

in Formula (E), R₃₁ represents a hydrogen atom or a substituted orunsubstituted alkyl group, Y₃₁ represents a chlorine atom, a hydroxylgroup, a substituted or unsubstituted amino group, or a morpholinogroup, M⁵ represents a hydrogen atom or a counter cation, M⁵′s may bethe same as or different from each other, and X₃₁ represents a grouprepresented by the following Formula (E-1), and

in Formula (E-1), R₃₂, R₃₃, R₃₄, R₃₅, and R₃₆ each independentlyrepresent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or—COOM′ (M′ represents a hydrogen atom or a counter cation), at least oneof R₃₂, R₃₃, R₃₄, R₃₅, or R₃₆ represents an alkyl group having 1 to 8carbon atoms or —COOM′, and * represents a direct bond to a carbon atom.2. The coloring composition according to claim 1, wherein X in Formula(A) represents a substituent represented by Formula (X1), and R⁴⁰¹,R⁴⁰², R⁴⁰³, R⁴⁰⁴, and R⁴⁰⁵ in Formula (X1) satisfy the condition (i). 3.The coloring composition according to claim 1, wherein X in Formula (A)represents a substituent represented by Formula (X2), and R⁵⁰¹, R⁵⁰²,R⁵⁰³, R⁵⁰⁴, R⁵⁰⁵, R⁵⁰⁶, and R⁵⁰⁷ in Formula (X2) satisfy the condition(iii).
 4. The coloring composition according to claim 1, wherein X inFormula (A) represents a substituent represented by Formula (X3), andR⁶⁰¹, R⁶⁰², R⁶⁰³, R⁶⁰⁴, R⁶⁰⁵, R⁶⁰⁶, and R⁶⁰⁷ in Formula (X3) satisfy thecondition (v).
 5. The coloring composition according to claim 1, whereina total content of a content of the compound represented by Formula (1),a content of the compound represented by Formula (D), and a content ofthe compound represented by Formula (E) is 2.0 to 5.0 mass % withrespect to the coloring composition.
 6. The coloring compositionaccording to claim 1, wherein in a case where the content of thecompound represented by Formula (1) is represented by W₁, the content ofthe compound represented by Formula (D) is represented by W_(D), and thecontent of the compound represented by Formula (E) is represented byW_(E), a mass ratio W₁/(W_(D)+W_(E)) is 90/10 to 60/40.
 7. An ink jetrecording ink comprising the coloring composition according to claim 1.8. An ink jet recording method using the ink jet recording ink accordingto claim
 7. 9. An ink jet printer cartridge that is filled with the inkjet recording ink according to claim 7.